Syn-selective silicon Mukaiyama-type aldol reactions of (pentafluoro-λ6-sulfanyl)acetic acid esters with aldehydes
Beilstein J. Org. Chem. 2018, 14, 373–380. doi:10.3762/bjoc.14.25
Supporting Information
| Supporting Information File 1: General procedure, synthesis of the aldol products, spectroscopic data, and copies of 1H, 13C, and 19F NMR spectra. | ||
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References
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- Full Research Paper
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Figure 1: Structures of GMIIb inhibitors.
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Scheme 1: Synthesis of pyrrolidines 2a and 3a.
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Scheme 2: Synthesis of pyrrolidines 2b,c and 3b,c.
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Scheme 3: Synthesis of pyrrolidines 4.
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Scheme 4: Synthesis of pyrrolidines 5.
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Figure 2: Molecular structure (OLEX2 drawing with adjacent ChemDraw image) of compound 20. Atomic displacemen...
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Scheme 1: Difunctionalization of double C=C bond with the formation of C–O and C–I bonds.
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Scheme 2: Iodo-oxyimidation of styrenes 1a–k with preparation of products 3aa–ka, 3ab–db, 3fb, 3hb, and 3kb.
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Figure 1: Scope of the iodo-oxyimidation of vinylarenes with I2/PhI(OAc)2 system. Reaction conditions: vinyla...
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Figure 2: Molecular structure of 3ca. Atoms are presented as anisotropic displacement parameters (ADP) ellips...
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Scheme 3: The proposed mechanism of iodo-oxyimidation of styrene (1a) using the NHPI/I2/PhI(OAc)2 system with...
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Figure 3: CV curves of styrene (1a, purple), NHPI (2a, red), I2 (blue) and PhI(OAc)2 (green) in 0.1 M n-Bu4NBF...
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Scheme 4: Gram-scale synthesis of compound 3aa.
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Scheme 5: Synthetic utility of the iodo-oxyimides 3aa and 3ab.
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Scheme 1: Triarylbismuth compounds, that serve as examples for the investigation of bismuth···π interactions ...
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Figure 1: Ball and stick model of a fragment of a) the zig-zag chain of a 1D arrangement of Ph3Bi (1a). Hydro...
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Figure 2: Ball and stick model of a fragment of the zig-zag type arrangement of Ph3Bi (1b) [45], view along the b...
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Figure 3: Ball and stick model of Ph3Bi (1c) showing: a) non-centrosymmetric dimers formed via two Bi···π are...
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Figure 4: Wire and stick representation of (C6H4-CH═CH2-4)3Bi (2a) showing: a) zig-zag chains of 1D ribbons f...
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Figure 5: Wire and stick model of (C6H4-CH═CH2-4)3Bi (2b) showing: a) the formation of 1D ribbons build via t...
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Figure 6: Molecular structure of (C6H4-OMe-4)3Bi (3) showing: a) Thermal ellipsoids that are set at 50% proba...
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Figure 7: Wire and stick model of (C6H3-t-Bu2-3,5)3Bi (4) showing a 3D network build via four C–Ht-Bu···π (ar...
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Figure 8: Wire and stick model of (C6H3-t-Bu2-3,5)2BiCl (5) showing a fragment of the 1D arrangement, view al...
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Figure 9: Computed interaction potentials of the distance scan for the idealized BiPh3–benzene complex. E(int...
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Figure 10: a) The BiPh3 potential energy curve for idealized interaction structures compared to the interactio...
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Figure 11: Structures of studied BiPh3 tetramers extracted from the crystal structure of polymorph 1a. Etetram...
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Figure 12: Detailed structures of selected dimers extracted from the crystal structure of polymorph 1a and dis...
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Figure 13: Structures of studied BiPh3 tetramers extracted from the crystal structure of polymorph 1b. See Figure 11 fo...
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Figure 14: Detailed structures of selected dimers extracted from the crystal structure of polymorph 1b and dis...
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Figure 15: Structures of studied BiPh3 tetramers extracted from the crystal structure of polymorph 1c. See Figure 11 fo...
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Figure 16: Detailed structures of selected dimers extracted from the crystal structure of the polymorph 1c and...
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Figure 17: Distortion energies of monomers (Eprep, blue triangles) and interaction energies of Bi···π and π-st...
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Figure 1: Cartoon representation of the chiral rotaxane of the Goldup group [15,16] (I and I*) and of the chiral pse...
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Figure 2: Cartoon representation of the rotaxane sequence isomers reported by Leigh [17] (III and IV) and of the ...
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Figure 3: The possible 8 discrete conformations of a calix[6]arene macrocycle [26].
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Figure 4: Diastereoisomeric pseudorotaxanes obtained by threading a directional calixarene wheel with directi...
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Scheme 1: Synthesis of threads 2+ and 3+. Reagents and conditions: a) hexamethyldisilazane, LiClO4, 30 min, 6...
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Figure 5: Possible mechanism for the formation of the two atropoisomeric pseudo[2]rotaxanes 2+
![[Graphic 2]](/bjoc/content/inline/1860-5397-14-186-i3.svg?max-width=637&scale=1.18182)
1cone and 2+11,...
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Figure 6: 1H NMR spectra (600 MHz, CDCl3, 298 K) of, from bottom to top: hexahexyloxycalix[6]arene 1; a 1:1 m...
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Figure 7: DFT-optimized structures of the: (left) 2+
1cone and (right) 2+11,2,3-alt pseudorotaxane atropoisome...
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Figure 8: The two pseudorotaxane atropoisomers obtained by threading hexahexyloxycalix[6]arene 1 with monosto...
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Figure 9: The two pseudorotaxane atropoisomers obtained by threading penta-O-methyl-p-tert-butylcalix[5]arene ...
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Figure 10: 1H NMR spectra (600 MHz, CDCl3, 298 K) of, from bottom to top: hexahexyloxycalix[6]arene 1; a 1:1 m...
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Figure 1: Hyperireflexolide A.
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Scheme 1: Retrosynthetic strategy.
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Scheme 2: Hydrolysis of dimethyl ketal 5.
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Scheme 3: Alkylation of γ-lactone-fused β-ketoester 6.
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Scheme 4: Synthesis of α,β-unsaturated ketone 11.
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Figure 1: Conversion of 1-substituted-4-formyltriazole analogs via ring-degenerate rearrangement of 1-substit...
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Figure 2: ORTEP structure of 2cc’. Thermal ellipsoids shown at 25% probability.
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Figure 3: 1H NMR aromatic region of a product mixture compared with reference imine analogs. Singlets appeari...
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Figure 4: Rearrangement reaction progress of 1a leading to irreversible formation of a colorimetric self-indi...
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Figure 1: Strategies for cobalt-catalyzed alkoxylation.
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Scheme 1: Reaction scope with respect to N-(naphthalen-1-yl)picolinamide derivatives. Reaction conditions: 1 ...
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Scheme 2: Reaction scope with respect to alcohols. Reaction conditions: 1a (0.2 mmol), 2 (1.0 mL), CoF2 (20 m...
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Scheme 3: Control experiments and mechanistic studies.
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Scheme 4: Proposed reaction mechanism.
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Scheme 5: Removal of the directing group.
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Figure 1: General structure of PHOX ligands 1 and structures of annulated glucosamine-based PHOX and PyOx lig...
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Scheme 1: Preparation of 1,2-isopropylidene-protected D-fructose derivatives with different substitution patt...
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Scheme 2: Activation of 7 to oxocarbenium ion 9 in the Ritter reaction.
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Scheme 3: Zemplén deacetylation of 10i.
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Figure 2: Molecular structure of 10j. Ellipsoids are given at the 50% probability level. Grey = carbon, red =...
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Scheme 4: Benzylation of 10j to give 10b.
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Scheme 5: Plausible mechanism of the Ritter reaction. For better clarity C-2 is not shown in conformers 9a an...
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Scheme 6: Neighboring group participation of ester protective groups. For better clarity C-2 is not shown in ...
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Scheme 7: Pd catalyzed Tsuji–Trost reation. BSA: N,O-bis(trimethylsilyl)acetamide, DMM: dimethyl malonate.
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Scheme 1: Chemical structures and acid-base stimuli responsiveness of target [2]rotaxane R1 and deprotonated ...
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Scheme 2: Syntheses of key intermediates 5, 8 and target [2]rotaxane R1.
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Figure 1: Partial 1H NMR spectra (400 MHz, CDCl3, 298 K). (a) Compound 5, (b) target [2]rotaxane R1, (c) azid...
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Figure 2: Partial 1H NMR spectra (400 MHz, CDCl3, 298 K). (a) [2]Rotaxane R1, (b) deprotonation by the additi...
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Figure 3: Partial 2D ROESY NMR spectra (500 MHz, CDCl3, 298 K). (a) [2]Rotaxane R1, (b) deprotonation with ad...
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Figure 1: Chemical structures of isosteric gelators 1 and 2 previously studied [33], and squaramide-based analogu...
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Scheme 1: Synthesis of squaramide-based gelators 3 and 4.
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Figure 2: Comparison of CGC, gelation time and Tgel values corresponding to six gels made using 3 and 2 [33] as g...
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Figure 3: DFS measurements for model gels made of 3 in methanol (c = 47 g/L) and ethyl acetate (c = 36 g/L). ...
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Figure 4: Representative FESEM images of selected xerogels prepared by freeze-drying the corresponding organo...
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Figure 1: Depiction of the energy levels of a typical organic molecule and the photophysical processes it can...
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Figure 2: General catalytic cycle of a photocatalyst in a photoredox organocatalysed reaction. [cat] – photoc...
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Figure 3: Structures and names of the most common photocatalysts encountered in the reviewed literature.
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Figure 4: General example of a reductive quenching catalytic cycle. [cat] – photocatalyst, [cat]* – photocata...
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Figure 5: General example of an oxidative quenching catalytic cycle. [cat] – photocatalyst, [cat]* – photocat...
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Scheme 1: Oxidative coupling of aldehydes and amines to amides using acridinium salt photocatalysis.
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Figure 6: Biologically active molecules containing a benzamide linkage.
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Scheme 2: The photocatalytic reduction of amino acids to produce the corresponding free or protected amines.
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Scheme 3: The organocatalysed photoredox base-mediated oxidation of thiols to disulfides.
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Scheme 4: C-Terminal modification of peptides and proteins using organophotoredox catalysis.
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Scheme 5: The reduction and aryl coupling of aryl halides using a doubly excited photocatalyst (PDI).
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Figure 7: Mechanism for the coupling of aryl halides using PDI, which is excited sequentially by two photons.
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Scheme 6: The arylation of five-membered heteroarenes using arenediazonium salts under organophotoredox condi...
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Scheme 7: The C–H (hetero)arylation of five-membered heterocycles under Eosin Y photocatalysis.
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Scheme 8: The C–H sulfurisation of imidazoheterocycles using Eosin B-catalyzed photochemical methods.
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Scheme 9: The introduction of the thiocyanate group using Eosin Y photocatalysis.
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Scheme 10: Sulfonamidation of pyrroles using oxygen as the terminal oxidant.
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Scheme 11: DDQ-catalysed C–H amination of arenes and heteroarenes.
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Scheme 12: Photoredox-promoted radical Michael addition reactions of allylic or benzylic carbons.
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Figure 8: Proposed mechanistic rationale for the observed chemoselectivities.
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Scheme 13: The photocatalytic manipulation of C–H bonds adjacent to amine groups.
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Scheme 14: The perylene-catalysed organophotoredox tandem difluoromethylation–acetamidation of styrene-type al...
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Figure 9: Examples of biologically active molecules containing highly functionalised five membered heterocycl...
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Scheme 15: The [3 + 2]-cycloaddition leading to the formation of pyrroles, through the reaction of 2H-azirines...
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Figure 10: Proposed intermediate that determines the regioselectivity of the reaction.
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Figure 11: Comparison of possible pathways of reaction and various intermediates involved.
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Scheme 16: The acridinium salt-catalysed formation of oxazoles from aldehydes and 2H-azirines.
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Scheme 17: The synthesis of oxazolines and thiazolines from amides and thioamides using organocatalysed photor...
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Figure 12: Biologically active molecules on the market containing 1,3,4-oxadiazole moieties.
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Scheme 18: The synthesis of 1,3,4-oxadiazoles from aldehyde semicarbazones using Eosin Y organophotocatalysis.
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Scheme 19: The dimerization of primary thioamides to 1,2,4-thiadiazoles catalysed by the presence of Eosin Y a...
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Scheme 20: The radical cycloaddition of o-methylthioarenediazonium salts and substituted alkynes towards the f...
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Scheme 21: The dehydrogenative cascade reaction for the synthesis of 5,6-benzofused heterocyclic systems.
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Figure 13: Trifluoromethylated version of compounds which have known biological activities.
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Scheme 22: Eosin Y-catalysed photoredox formation of 3-substituted benzimidazoles.
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Scheme 23: Oxidation of dihydropyrimidines by atmospheric oxygen using photoredox catalysis.
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Scheme 24: Photoredox-organocatalysed transformation of 2-substituted phenolic imines to benzoxazoles.
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Scheme 25: Visible light-driven oxidative annulation of arylamidines.
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Scheme 26: Methylene blue-photocatalysed direct C–H trifluoromethylation of heterocycles.
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Scheme 27: Photoredox hydrotrifluoromethylation of terminal alkenes and alkynes.
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Scheme 28: Trifluoromethylation and perfluoroalkylation of aromatics and heteroaromatics.
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Scheme 29: The cooperative asymmetric and photoredox catalysis towards the functionalisation of α-amino sp3 C–...
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Scheme 30: Organophotoredox-catalysed direct C–H amidation of aromatics.
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Scheme 31: Direct C–H alkylation of heterocycles using BF3K salts. CFL – compact fluorescent lamp.
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Figure 14: The modification of camptothecin, demonstrating the use of the Molander protocol in LSF.
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Scheme 32: Direct C–H amination of aromatics using acridinium salts.
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Scheme 33: Photoredox-catalysed nucleophilic aromatic substitution of nucleophiles onto methoxybenzene derivat...
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Scheme 34: The direct C–H cyanation of aromatics with a focus on its use for LSF.
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Scheme 1: Synthesis of half-sandwich rhodium metallarectangles via three different methods. Method A: coordin...
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Figure 1: Partial 1H NMR spectra (400 MHz, DMSO-d6, ppm) of (a) L1; (b) the sample of metallarectagle 3a obta...
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Figure 2: Partial 1H NMR spectra (400 MHz, DMSO-d6, ppm) of (a) L2; (b) a sample of metallarectangle 3b obtai...
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Figure 3: Calculated (bottom) and experimental (top) ESI-MS spectra of the tetracationic half-sandwich rhodiu...
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Figure 4: Optimized structures of the charged metallarectangles 3a (top) and 3b (bottom), optimized with the ...
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Figure 1: Partial structure [7,8] of the (a) graphene oxide (GO) and (b) reduced graphene oxide (RGO).
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Figure 2: Mechanism of the amidation/esterification-type reactions with the GO/RGO using carbodiimide and N-h...
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Figure 3: Mechanism of the Steglich esterification with the GO/RGO: (a) acid–base reaction of the carboxyl gr...
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Figure 4: Mechanism of the epoxide ring opening reaction with the GO/RGO.
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Figure 5: Generation of the free amine (nucleophile) from the corresponding amine hydrohalide using an acid–b...
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Figure 6: Mechanism of amidation/esterification-type reactions with the GO/RGO using 1,1’-carbonyldiimidazole...
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Figure 7: Mechanism of the covalent functionalization of graphene-family material applying diazonium salts ch...
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Figure 1: Precedent examples of catalytic allylic C(sp3)–H additions to carbonyl electrophiles.
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Figure 2: Substrate scope for acetophenone derivatives. aPreparative scale synthesis using 1 mmol of 2a.
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Figure 3: Substrate scope for α-olefins.
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Figure 4: A possible catalytic cycle.
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Figure 1: Examples of chiral bimetallic complexes utilized in asymmetric catalysis.
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Figure 2: Previously reported bisoxazoline ligands capable of stabilizing bimetallic complexes.
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Scheme 1: Synthesis of naphthyridine–bisoxazoline ligand 16-H2.
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Figure 3: Thermal ellipsoid plot (50% probability) of the molecular structure of 16·Ni2(OAc)2. Hydrogen and s...
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Scheme 2: Synthesis of naphthyridine–bisoxazoline ligand 22-H2.
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Scheme 3: Synthesis of pyrazole–bisoxazoline ligand 25-H3.
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Figure 4: Thermal ellipsoid plot (50% probability) of the molecular structure of 25·Ni2(OAc). Hydrogen and so...
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Scheme 4: Synthesis of pyrazole–bisoxazoline ligand 30-H3.
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Figure 5: Thermal ellipsoid plot (50% probability) of the molecular structure of 30·Pd2Br. Hydrogen and solva...
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Scheme 5: Synthesis of pyridazine–bisoxazoline ligand 32-H2.
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Figure 6: Thermal ellipsoid plot (50% probability) of the molecular structure of 32·Zn2Cl2. Hydrogen and solv...
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Scheme 6: Synthesis of phenol–bisoxazoline ligand 34-H3.
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Scheme 1: The preparation of compound 3.
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Figure 1: The chemical structure and the schematic representation of compound 3 as well as the proposed assem...
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Figure 2: UV–vis absorbance spectra of a) compound 3 and b) irradiated by a light source of 365 nm and c) the...
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Figure 3: CD spectrum of compound 3 in solutions of a) benzene, toluene, p-xylene, chloroform, tetrachloromet...
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Figure 4: SEM images of the microstructure a) obtained by the self-assembled compound 3 in CHCl3 on the surfa...
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Figure 5: a) The gel-to-sol transformation of the samples via different routes. b) Dynamic frequency sweep of...
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Scheme 1: The general structure of triazolylcalix[4]arene derivatives.
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Scheme 2: Synthesis of di- (4a,b) and tetraazido (8a,b) calix[4]arene derivatives. Conditions: Ia: AlkBr, K2CO...
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Figure 1: Molecular structure of 8a (50% ellipsoids). The dashed line indicates the alternative position of t...
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Scheme 3: Synthesis of polyammonium macrocycles 10a,b and 12a,b.
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Figure 2: 2D NOESY H1-H1 NMR spectra of 10b in DMSO-d6.
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Figure 3: The optical response (OR) of the calixarene/EY systems toward adenosine phosphates. Concentration (...
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Figure 4: Supramolecular binding motif of diphosphate (a) and triphosphate (b) groups of nucleotides with the...
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Figure 5: UV spectra of EY (1), 10b–EY (2), and 10b–EY in the presence of 0.005 (3), 0.05 (4), 0.5 (5) and 2 ...
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Scheme 4: Structure of AEPDA and the corresponding AEPCDA–10b polydiacetylene vesicle.
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Figure 6: UV spectra of the AEPCDA polydiacetylene vesicles in the presence of different amounts of 10b; conc...
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Figure 7: Photographs of a portion of a 96-well plate containing AEPCDA–10b polydiacetylene vesicles in the a...
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Scheme 1: ortho-Aminophenol derivatives.
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Scheme 2: Rearrangement of N-acyloxyanilines.
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Scheme 3: Mechanistic studies, reported in [13].
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Scheme 4: Competitive experiments, reported in [13].
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Scheme 5: Mechanism for rearrangement to the para-position.
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Figure 1: a) The “anchor group” approach for a rational design of CB–dye pairs involving a thermodynamic cycl...
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Scheme 1: Synthesis of BODIPY derivatives.
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Figure 2: a) Normalized absorption (solid line) and normalized fluorescence emission spectrum (dotted line) o...
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Figure 3: a) Fluorescence spectral changes (λexc = 470 nm) upon addition of CB7 to 50 nM 1 in 10 mM citrate b...
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Figure 4: Fluorescence pH titration of 2 and the respective complex (in presence of 3 mM CB7) in 30% (v/v) AC...
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Figure 5: Fluorescence displacement titrations (λex = 470 nm, λem = 510 nm). a) 5 µM 2 and 2.5 µM CB7 with cy...
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Figure 6: FCS autocorrelation curves obtained with 10 nM 2 in the absence (red fitted line) and presence (blu...
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Figure 7: Fluorescence microscopy images of 1 mg/mL polymer microspheres a) with or b) without surface-bound ...
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Scheme 1: Synthesis of “earring” subporphyrin and its Pd complex. Synthetic procedure: (i) Diboryltripyrrane ...
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Figure 1: Partial 1H NMR spectrum of 3.
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Figure 2: X-ray crystal structures of 3: a) top view; b) side view. Thermal ellipsoids are drawn at the 50% p...
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Figure 3: Partial 1H NMR spectrum of 3Pd.
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Figure 4: X-ray crystal structures of 3Pd: a) top view; b) side view. Thermal ellipsoids are at the 30% proba...
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Figure 5: UV–vis/NIR spectra of 3 and 3Pd.
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Figure 1: Schematic illustration of possible support-assisted methods.
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Figure 2: Expected reactivity of 5’- and 3’-terminus for the activation.
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Scheme 1: Competition experiment between alcohol and carboxylic acid. Reagents and conditions: (i) 4-phenylbu...
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Scheme 2: Conjugation between the 5’-activated supported trinucleotide 2 and the tripeptide 3. Reagents and c...
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Figure 3: HPLC spectra of the crude protected bioconjugate 4 and the crude deprotected bioconjugate 5.
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Scheme 3: 5’-Phosphitylation of supported decanucleotide 13. Reagents and conditions: 2-cyanoethyl-N,N,N',N'-...
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Scheme 4: Conjugation between 5’-activated supported decanucleotide 14 and supported pentapeptide 7. Reagents...
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Figure 4: HPLC spectra of the crude protected bioconjugate 15 and the deprotected bioconjugate 16.
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Figure 1: Chemical structures of (a) tri(ethylene oxide)-substituted pillar[n]arenes (1, n = 5; 2, n = 6), (b...
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Figure 2: 1H NMR spectra of (a) model compound 4 (2 mM at 25 °C in CDCl3), (b) 3 (2 mM at 25 °C in CDCl3), (c...
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Figure 3: Temperature dependence of light transmittance at 650 nm of an aqueous solution of (a) 3 (2 mM) upon...
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Figure 4: Photographs of (a) 3 and (c) a mixture of 3 (2 mM) and 1,4-dicyanobutane (20 mM) in aqueous media a...
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Scheme 1: Synthesis of the bicyclic compound 3.
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Supp. Info
- Review
- Published 26 Jul 2018
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Graphical Abstract
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Figure 1: Key features of different approaches for unified multistep synthesis platform.
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Figure 2: Schematic representation of a unified platform for the flow synthesis (P1–P14 pumps, PBR packed bed...
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Figure 3: Layout of a unified synthesis platform (including all the component) for multiple drug molecules (a...
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Figure 4: Layout for synthesis of 4 molecules on a single platform (approach 2).
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Scheme 1: The overall process for the synthesis of diphenhydramine hydrochloride.
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Figure 5: Approach 3 for a unified platform for multistep synthesis. M1–M9 = mixers, R1–R4 = tubular reactors...
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- Full Research Paper
- Published 25 Jul 2018
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Graphical Abstract
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Figure 1: Two [2]rotaxane molecular shuttles with both bis(pyridinium)ethane and benzylanilinium recognition ...
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Figure 2: A [3]catenane containing two identical bis(pyridinium)ethane recognition sites on a large macrocycl...
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Scheme 1: Step-wise synthesis of [2]catenane [8
![[Graphic 3]](/bjoc/content/inline/1860-5397-14-165-i4.svg?max-width=637&scale=0.827274)
DB24C8]6+ containing benzylanilinium and bis(pyridinium)ethane...
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Figure 3: 1H NMR spectrum of [2]catenane [8
DB24C8]6+ (500 MHz, 298 K, CD2Cl2) showing the assigned proton che...
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Figure 4: a) The [2]catenane [8
DB24C8]6+ can be protonated to yield [8-HDB24C8]7+ in two different co-conform...
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Figure 5: UV–visible spectra of [8
DB24C8]6+ (orange trace) and [8-HDB24C8]7+ (black trace) in CH3CN solution ...
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