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6 article(s) from Neudörfl, Jörg M

Silanediol versus chlorosilanol: hydrolyses and hydrogen-bonding catalyses with fenchole-based silanes

Falco Fox,
Jörg M. Neudörfl and
Bernd Goldfuss

Beilstein J. Org. Chem. 2019, 15, 167–186, doi:10.3762/bjoc.15.17

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Figure 1: Hydrogen-bonding silanediols, i.e., di(1-naphthyl)silanediol (1) [39], silanediols 2 [41-43], binaphthylsilane...

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Scheme 1: Hydrogen-bond-catalyzed N-acyl Mannich reaction of in situ-generated isoquinolin derivative 10 with...

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Scheme 2: Synthesis of BIFOXSiCl₂, starting with BIFOL (5) [52,54] yielding dichlorosilane 7.

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Scheme 3: Hydrolysis of BIFOXSiCl₂ (7) yielding the corresponding silanediol 9 and controlled hydrolysis of B...

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Scheme 4: Hydrolysis of dichlorosilanes 13 and 14 to their corresponding silanediols 1 and 15 [51,60].

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Figure 2: Hydrolyses of dichlorosilane 7 and 14 to BIFOXSi(OH)₂ (9, green circle) and bis(2,4,6-tri-tert-buty...

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Figure 3: Hydrolyses of BIFOXSiCl₂ (7) to BIFOXSi(OH)₂ (9, green circle), bis(2,4,6-tri-tert-butylphenoxy)dic...

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Scheme 5: Two investigated pathways for the hydrolysis of the dichlorosilanes. Front attack mechanism (front)...

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Figure 4: Three transition structures each, for the hydrolysis of BIFOXSiCl₂ (7) and BIFOXSiCl(OH) (8) consid...

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Figure 5: Computed hydrolyses of BIFOXSiCl₂ (7) to BIFOXSiCl(OH) 8_ax and BIFOXSiCl(OH) 8_eq and subsequent com...

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Figure 6: Transition state leading to 8_eq following front1 attack (E_a = 32.6 kcal mol⁻¹, Figure 5, Table 3, entry 1). Breaki...

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Figure 7: Transition state leading to 8_ax following front2 attack (E_a = 33.2 kcal mol⁻¹, Figure 5, Table 3, entry 2). Breaki...

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Figure 8: Transition state leading to 8_eq following side attack (E_a = 37.4 kcal mol⁻¹, Figure 5, Table 3, entry 3). Breaking...

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Figure 9: Transition state leading to 9 following side attack (E_a = 31.4 kcal mol⁻¹, Figure 5, Table 3, entry 6). Breaking a...

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Figure 10: Transition state leading to 9 following front1 attack (E_a = 33.4 kcal mol⁻¹, Figure 5, Table 3, entry 4). Breaking...

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Figure 11: Transition state leading to 9 following front2 attack (E_a = 40.2 kcal mol⁻¹, Figure 5, Table 3, entry 5). Breaking...

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Figure 12: X-ray crystal structure of BIFOXSiCl₂ (7). H atoms on the chiral backbone are omitted for clarity i...

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Figure 13: X-ray crystal structure of BIFOXSiCl(OH) (8). H atoms on the chiral backbone are omitted for clarit...

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Figure 14: X-ray crystal structure ofrac-BIFOXSi(OH)₂ (9) forming dimers. H atoms on the chiral backbone are o...

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Figure 15: X-ray crystal structure of BIFOXSi(OH)₂ (9) forming a tetramer. H atoms on the chiral backbone are ...

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Figure 16: X-ray crystal structure of BIFOXSi(OH)₂ (9) forming a dimeric structure with two bridged acetone mo...

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Figure 17: X-ray crystal structure of BIFOXSiCl(OH) (8), binding an acetone molecule. H atoms on the chiral ba...

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Scheme 6: Hydrogen-bond-catalyzed N-acyl Mannich reaction of in situ-generated 10 with different silyl ketene...

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Scheme 7: Hydrogen-bond-catalyzed nucleophilic substitution of 18 with BIFOXSi(OH)₂ (9) and nucleophile silyl...

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Scheme 8: Nucleophilic substitution of 20 with BIFOXSi(OH)₂ (9) and nucleophile silyl ketene acetals 11, 20 a...

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Published 18 Jan 2019

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An unusually stable chlorophosphite: What makes BIFOP–Cl so robust against hydrolysis?

Roberto Blanco Trillo,
Jörg M. Neudörfl and
Bernd Goldfuss

Beilstein J. Org. Chem. 2015, 11, 313–322, doi:10.3762/bjoc.11.36

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Scheme 1: Fenchyl-based ligands used as building blocks for phosphorous ligands or organoaluminum reagents.

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Scheme 2: Reaction of BIFOP–Cl (1) to BIFOP–(O)H (2) and of O–BIFOP–Cl (3) yielding O–BIFOP–H (4), O–BIFOP–(O...

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Figure 1: ³¹P NMR (125 MHz, CDCl₃) of O–BIFOP–Cl (3, δ = 161.9) after the addition of 1 equiv H₂O and formati...

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Figure 2: X-ray crystal structure of diphenyl ether-2,2’-biscyclofenchene 7. Ellipsoids are shown with 50% pr...

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Scheme 3: Proposed mechanism for the formation of diphenyl ether-2,2’-biscyclofenchene 7 through stabilizatio...

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Figure 3: ³¹P NMR (125 MHz, CDCl₃) of O–BIFOP–H (4, δ = 152.5) adding O₂ after a) 5 min; b) 15 min; c) 120 mi...

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Figure 4: X-ray crystal structure of BIFOP-Cl 1. Ellipsoids are shown with 50% probability [15].

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Scheme 4: The different backbones provoke different reactivities due to tighter encapsulation of the P–Cl uni...

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Figure 5: X-ray crystal structure of O-BIFOP-Cl (3). Ellipsoids are shown with 50% probability.

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Figure 6: Transition state structure for the reaction of BIFOP–Cl (1) with water (BP86/def-SV(P)).

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Figure 7: Transition state structure for the reaction of O-BIFOP–Cl (3) with water (BP86/def-SV(P)).

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Published 04 Mar 2015

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New hydrogen-bonding organocatalysts: Chiral cyclophosphazanes and phosphorus amides as catalysts for asymmetric Michael additions

Helge Klare,
Jörg M. Neudörfl and
Bernd Goldfuss

Beilstein J. Org. Chem. 2014, 10, 224–236, doi:10.3762/bjoc.10.18

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Figure 1: Thiourea, squaramide, P-triamide and cyclodiphosphazane with computed distances between H-atoms.

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Figure 2: Urea, squaramide, P-triamide and cyclodiphosphazane coordinated to nitrobenzene, with the computed ...

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Scheme 1: Chiral P^V-amide catalysts based on BINOL and chinchona backbones.

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Scheme 2: Exclusive formation of the mono- and trisubstituted product from thiophosphoryl chloride and anilin...

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Figure 3: X-ray structure of 6-dimer. The hydrogen atoms are omitted for clarity, except at all nitrogens.

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Figure 4: X-ray structure of 7a-dimer. The hydrogen atoms are omitted for clarity, except at all nitrogens.

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Scheme 3: Synthesis of chiral cyclodiphosphazane catalysts 14a/b, 15 and 16.

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Figure 5: X-ray structure of 14a. The hydrogen atoms are omitted for clarity, except at nitrogen.

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Figure 6: ³¹P{1H} NMR spectrum in CDCl₃ at rt showing C₂ symmetry of 14a at rt.

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Figure 7: X-ray structure of 15. The hydrogen atoms are omitted for clarity, except at nitrogen.

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Figure 8: X-ray structure of 16. The hydrogen atoms are omitted for clarity, except at nitrogen.

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Figure 9: Enantiodetermining transition states TS-14a/TS-14b arising from the addition of 2-hydroxynapthoquin...

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Published 21 Jan 2014

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Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions

Matthias Leven,
Jörg M. Neudörfl and
Bernd Goldfuss

Beilstein J. Org. Chem. 2013, 9, 155–165, doi:10.3762/bjoc.9.18

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Scheme 1: Activation of amine-bonded Michael acceptors by protonation versus Lewis acid interaction.

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Scheme 2: Synthesis of 4-hydroxycoumarin derivatives by Michael addition [19-27].

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Scheme 3: Precatalysts 5–8 and synthesis from chiral 1,2-diamines and 2-sulfobenzoic anhydrides.

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Figure 1: X-ray crystallographic structure of 5. The conformation of the 2-sulfobenzoic moiety is fixed by hy...

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Figure 2: Michael acceptors employed as substrates in the nucleophilic addition of 4-hydroxycoumarin (1).

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Scheme 4: Computationally analyzed pathways A (C-protonation), and B (N-protonation), arising from the additi...

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Scheme 5: Computed energy profile for reaction path A (C-protonation) and B (N-protonation) corresponding to ...

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Figure 3: Enantio-determining transition states arising from the addition of 4-hydroxycoumarin to cyclohexeno...

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Figure 4: The competing enantio-determining transition structures TS-14a and TS-14g. The reason for the desta...

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Published 23 Jan 2013

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Lithium phosphonate umpolung catalysts: Do fluoro substituents increase the catalytic activity?

Anca Gliga,
Bernd Goldfuss and
Jörg M. Neudörfl

Beilstein J. Org. Chem. 2011, 7, 1189–1197, doi:10.3762/bjoc.7.138

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Scheme 1: Proposed catalytic cycle of the lithium phosphonate catalyzed cross benzoin coupling [18].

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Scheme 2: Phosphonate as precatalysts in benzoin coupling [18,26].

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Scheme 3: Synthesis of diols 1–4, 6–7; diol 5 is commercially available.

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Figure 1: X-ray crystal structure of 6. (M)-(S,S) and (P)-(R,R) pair of enantiomers; intermolecular O1–O2 dis...

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Figure 2: X-ray crystal structure of 7. (M)-(S,S) and (P)-(R,R) pair of enantiomers; intermolecular O1–O2 dis...

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Scheme 4: Synthesis of phosphonates 9–15.

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Figure 3: ³¹P NMR of phosphonate 14 (a) and 15 (b).

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Figure 4: X-ray crystal structure of 15. (M)-(R,S) diastereomer; ellipsoids correspond to 50% probability lev...

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Scheme 5: Lithium phosphonate catalysts in cross benzoin coupling.

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Figure 5: Phosphonate precatalysts 9–15 in cross benzoin coupling.

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Published 31 Aug 2011

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Synthesis of spiroannulated and 3-arylated 1,2,4-trioxanes from mesitylol and methyl 4-hydroxytiglate by photooxygenation and peroxyacetalization

Axel G. Griesbeck,
Lars-Oliver Höinck and
Jörg M. Neudörfl

Beilstein J. Org. Chem. 2010, 6, No. 61, doi:10.3762/bjoc.6.61

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Figure 1: Antimalaria active natural artemisinin 1 and the spirobicyclic 1,2,4-trioxane derivative 2 show the...

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Scheme 1: Singlet oxygen ene reaction of methyl 4-hydroxytiglate (3) and mesitylol (6) under solid-phase cond...

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Scheme 2: 1,2,4-trioxane 9c and bis-trioxane 8a,b formation from the bifunctional cyclohexa-1,4-dione.

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Figure 2: Structure of the spirobicyclic trioxane 5c in the crystal.

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Scheme 3: BF₃-catalyzed acetalization of hydroperoxide 4 with benzaldehyde derivatives.

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Figure 3: Structure of the 3-arylated trioxane 10b in the crystal.

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Figure 4: Structure of the p-bromophenyl derivative 10d in the crystal lattice (disordered water molecules in...

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Figure 5: Numbering of 3-aryl-1,2,4-trioxanes 10 and relevant bonds; structure of artemether (AM).

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Published 07 Jun 2010

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