Catalytic multi-step domino and one-pot reactions
Friedrich-Alexander-Universität Erlangen-Nürnberg
In particular, catalytic domino reactions and one-pot processes with excellent selectivity and functional group tolerance are of significant interest for industrial and academic research alike. Such processes, using conventional reagents and also visible light, can simplify the synthesis of pharmaceutical ingredients and drugs. In these so-called domino reactions, all of the required reagents, the catalyst and a solvent are simply mixed in one flask, in which multiple reaction steps take place autonomously without the addition of further reactants. This strategy is in contrast to the conventional "stop-and-go" synthetic approach. These efficient and straightforward synthetic methods make the isolation and purification of intermediate products after each reaction step superfluous, thereby drastically reducing the number of work-up and purification steps, which is superior to conventional organic synthesis.
For this thematic issue, contributions on all types of catalytic multi-step domino and one-pot reactions are welcome.
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Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones
- Manuel Pedrón,
- Jana Sendra,
- Irene Ginés,
- Tomás Tejero,
- Jose L. Vicario and
- Pedro Merino
Beilstein J. Org. Chem. 2023, 19, 477–486, doi:10.3762/bjoc.19.37
Graphical Abstract
Scheme 1: Experimental data (series a–d, k) and non-studied examples (series e–j) for transannular cycloaddit...
Figure 1: Optimized (m062x/6-31G(d)) geometries for the transition structures of series a–f.
Figure 2: Top: Cycloaddition of protonated hydrazones as inverse-demand reaction of cycloaddition of azomethi...
Figure 3: Global electron density transfer (GEDT). Dashed black line indicates both TS.
Figure 4: ELF analysis for the reaction of series b leading to a system 6-6. Black trace corresponds to IRC. ...
Figure 5: Quantitative NCI analysis [36] for the reaction of series a–f leading to fused cyclohexanes. The result...
Figure 6: (a) Transannular cycloadditons of compounds 1a–k. (b) Houk’s distortion model applied to the reacti...
Scheme 2: Reaction with simple models.
Transition-metal-catalyzed domino reactions of strained bicyclic alkenes
- Austin Pounder,
- Eric Neufeld,
- Peter Myler and
- William Tam
Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38
Graphical Abstract
Figure 1: Ring-strain energies of homobicyclic and heterobicyclic alkenes in kcal mol−1. a) [2.2.1]-Bicyclic ...
Figure 2: a) Exo and endo face descriptions of bicyclic alkenes. b) Reactivity comparisons for different β-at...
Scheme 1: Ni-catalyzed ring-opening/cyclization cascade of heterobicyclic alkenes 1 with alkyl propiolates 2 ...
Scheme 2: Ni-catalyzed ring-opening/cyclization cascade of heterobicyclic alkenes 8 with β-iodo-(Z)-propenoat...
Scheme 3: Ni-catalyzed two- and three-component difunctionalizations of norbornene derivatives 15 with alkyne...
Scheme 4: Ni-catalyzed intermolecular three-component difunctionalization of oxabicyclic alkenes 1 with alkyn...
Scheme 5: Ni-catalyzed intermolecular three-component carboacylation of norbornene derivatives 15.
Scheme 6: Photoredox/Ni dual-catalyzed coupling of 4-alkyl-1,4-dihydropyridines 31 with heterobicyclic alkene...
Scheme 7: Photoredox/Ni dual-catalyzed coupling of α-amino radicals with heterobicyclic alkenes 30.
Scheme 8: Cu-catalyzed rearrangement/allylic alkylation of 2,3-diazabicyclo[2.2.1]heptenes 47 with Grignard r...
Scheme 9: Cu-catalyzed aminoboration of bicyclic alkenes 1 with bis(pinacolato)diboron (B2pin2) (53) and O-be...
Scheme 10: Cu-catalyzed borylalkynylation of oxabenzonorbornadiene (30b) with B2pin2 (53) and bromoalkynes 62.
Scheme 11: Cu-catalyzed borylacylation of bicyclic alkenes 1.
Scheme 12: Cu-catalyzed diastereoselective 1,2-difunctionalization of oxabenzonorbornadienes 30 for the synthe...
Scheme 13: Fe-catalyzed carbozincation of heterobicyclic alkenes 1 with arylzinc reagents 74.
Scheme 14: Co-catalyzed addition of arylzinc reagents of norbornene derivatives 15.
Scheme 15: Co-catalyzed ring-opening/dehydration of oxabicyclic alkenes 30 via C–H activation of arenes.
Scheme 16: Co-catalyzed [3 + 2] annulation/ring-opening/dehydration domino reaction of oxabicyclic alkenes 1 w...
Scheme 17: Co-catalyzed enantioselective carboamination of bicyclic alkenes 1 via C–H functionalization.
Scheme 18: Ru-catalyzed cyclization of oxabenzonorbornene derivatives with propargylic alcohols for the synthe...
Scheme 19: Ru-catalyzed coupling of oxabenzonorbornene derivatives 30 with propargylic alcohols and ethers 106...
Scheme 20: Ru-catalyzed ring-opening/dehydration of oxabicyclic alkenes via the C–H activation of anilides.
Scheme 21: Ru-catalyzed of azabenzonorbornadiene derivatives with arylamides.
Scheme 22: Rh-catalyzed cyclization of bicyclic alkenes with arylboronate esters 118.
Scheme 23: Rh-catalyzed cyclization of bicyclic alkenes with dienyl- and heteroaromatic boronate esters.
Scheme 24: Rh-catalyzed domino lactonization of doubly bridgehead-substituted oxabicyclic alkenes with seconda...
Scheme 25: Rh-catalyzed domino carboannulation of diazabicyclic alkenes with 2-cyanophenylboronic acid and 2-f...
Scheme 26: Rh-catalyzed synthesis of oxazolidinone scaffolds 147 through a domino ARO/cyclization of oxabicycl...
Scheme 27: Rh-catalyzed oxidative coupling of salicylaldehyde derivatives 151 with diazabicyclic alkenes 130a.
Scheme 28: Rh-catalyzed reaction of O-acetyl ketoximes with bicyclic alkenes for the synthesis of isoquinoline...
Scheme 29: Rh-catalyzed domino coupling reaction of 2-phenylpyridines 165 with oxa- and azabicyclic alkenes 30....
Scheme 30: Rh-catalyzed domino dehydrative naphthylation of oxabenzonorbornadienes 30 with N-sulfonyl 2-aminob...
Scheme 31: Rh-catalyzed domino dehydrative naphthylation of oxabenzonorbornadienes 30 with arylphosphine deriv...
Scheme 32: Rh-catalyzed domino ring-opening coupling reaction of azaspirotricyclic alkenes using arylboronic a...
Scheme 33: Tandem Rh(III)/Sc(III)-catalyzed domino reaction of oxabenzonorbornadienes 30 with alkynols 184 dir...
Scheme 34: Rh-catalyzed asymmetric domino cyclization and addition reaction of 1,6-enynes 194 and oxa/azabenzo...
Scheme 35: Rh/Zn-catalyzed domino ARO/cyclization of oxabenzonorbornadienes 30 with phosphorus ylides 201.
Scheme 36: Rh-catalyzed domino ring opening/lactonization of oxabenzonorbornadienes 30 with 2-nitrobenzenesulf...
Scheme 37: Rh-catalyzed domino C–C/C–N bond formation of azabenzonorbornadienes 30 with aryl-2H-indazoles 210.
Scheme 38: Rh/Pd-catalyzed domino synthesis of indole derivatives with 2-(phenylethynyl)anilines 212 and oxabe...
Scheme 39: Rh-catalyzed domino carborhodation of heterobicyclic alkenes 30 with B2pin2 (53).
Scheme 40: Rh-catalyzed three-component 1,2-carboamidation reaction of bicyclic alkenes 30 with aromatic and h...
Scheme 41: Pd-catalyzed diarylation and dialkenylation reactions of norbornene derivatives.
Scheme 42: Three-component Pd-catalyzed arylalkynylation reactions of bicyclic alkenes.
Scheme 43: Three-component Pd-catalyzed arylalkynylation reactions of norbornene and DFT mechanistic study.
Scheme 44: Pd-catalyzed three-component coupling N-tosylhydrazones 236, aryl halides 66, and norbornene (15a).
Scheme 45: Pd-catalyzed arylboration and allylboration of bicyclic alkenes.
Scheme 46: Pd-catalyzed, three-component annulation of aryl iodides 66, alkenyl bromides 241, and bicyclic alk...
Scheme 47: Pd-catalyzed double insertion/annulation reaction for synthesizing tetrasubstituted olefins.
Scheme 48: Pd-catalyzed aminocyclopropanation of bicyclic alkenes 1 with 5-iodopent-4-enylamine derivatives 249...
Scheme 49: Pd-catalyzed, three-component coupling of alkynyl bromides 62 and norbornene derivatives 15 with el...
Scheme 50: Pd-catalyzed intramolecular cyclization/ring-opening reaction of heterobicyclic alkenes 30 with 2-i...
Scheme 51: Pd-catalyzed dimer- and trimerization of oxabenzonorbornadiene derivatives 30 with anhydrides 268.
Scheme 52: Pd-catalyzed Catellani-type annulation and retro-Diels–Alder of norbornadiene 15b yielding fused xa...
Scheme 53: Pd-catalyzed hydroarylation and heteroannulation of urea-derived bicyclic alkenes 158 and aryl iodi...
Scheme 54: Access to fused 8-membered sulfoximine heterocycles 284/285 via Pd-catalyzed Catellani annulation c...
Scheme 55: Pd-catalyzed 2,2-bifunctionalization of bicyclic alkenes 1 generating spirobicyclic xanthone deriva...
Scheme 56: Pd-catalyzed Catellani-type annulation and retro-Diels–Alder of norbornadiene (15b) producing subst...
Scheme 57: Pd-catalyzed [2 + 2 + 1] annulation furnishing bicyclic-fused indanes 281 and 283.
Scheme 58: Pd-catalyzed ring-opening/ring-closing cascade of diazabicyclic alkenes 130a.
Scheme 59: Pd-NHC-catalyzed cyclopentannulation of diazabicyclic alkenes 130a.
Scheme 60: Pd-catalyzed annulation cascade generating diazabicyclic-fused indanones 292 and indanols 294.
Scheme 61: Pd-catalyzed skeletal rearrangement of spirotricyclic alkenes 176 towards large polycyclic benzofur...
Scheme 62: Pd-catalyzed oxidative annulation of aromatic enamides 298 and diazabicyclic alkenes 130a.
Scheme 63: Accessing 3,4,5-trisubstituted cyclopentenes 300, 301, 302 via the Pd-catalyzed domino reaction of ...
Scheme 64: Palladacycle-catalyzed ring-expansion/cyclization domino reactions of terminal alkynes and bicyclic...
Scheme 65: Pd-catalyzed carboesterification of norbornene (15a) with alkynes, furnishing α-methylene γ-lactone...
Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles
- Péter Kisszékelyi and
- Radovan Šebesta
Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44
Graphical Abstract
Scheme 1: General scheme depicting tandem reactions based on an asymmetric conjugate addition followed by an ...
Scheme 2: Cu-catalyzed tandem conjugate addition of R2Zn/aldol reaction with chiral acetals.
Scheme 3: Cu-catalyzed asymmetric desymmetrization of cyclopentene-1,3-diones using a tandem conjugate additi...
Scheme 4: Stereocontrolled assembly of dialkylzincs, cyclic enones, and sulfinylimines utilizing a Cu-catalyz...
Scheme 5: Cu-catalyzed tandem conjugate addition/Mannich reaction (A). Access to chiral isoindolinones and tr...
Scheme 6: Cu-catalyzed tandem conjugate addition/nitro-Mannich reaction (A) with syn–anti or syn–syn selectiv...
Figure 1: Various chiral ligands utilized for the tandem conjugate addition/Michael reaction sequences.
Scheme 7: Cu-catalyzed tandem conjugate addition/Michael reaction: side-product formation with chalcone (A) a...
Scheme 8: Zn enolate trapping using allyl iodides (A), Stork–Jung vinylsilane reagents (B), and allyl bromide...
Scheme 9: Cu-catalyzed tandem conjugate addition/acylation through Li R2Zn enolate (A). A four-component coup...
Scheme 10: Selected examples for the Cu-catalyzed tandem conjugate addition/trifluoromethylthiolation sequence....
Scheme 11: Zn enolates trapped by vinyloxiranes: synthesis of allylic alcohols.
Scheme 12: Stereoselective cyclopropanation of Mg enolates formed by ACA of Grignard reagents to chlorocrotona...
Scheme 13: Domino aldol reactions of Mg enolates formed from coumarin and chromone.
Scheme 14: Oxidative coupling of ACA-produced Mg enolates.
Scheme 15: Tandem ACA of Grignard reagents to enones and Mannich reaction.
Scheme 16: Diastereodivergent Mannich reaction of Mg enolates with differently N-protected imines.
Scheme 17: Tandem Grignard–ACA–Mannich using Taddol-based phosphine-phosphite ligands.
Scheme 18: Tandem reaction of Mg enolates with aminomethylating reagents.
Scheme 19: Tandem reaction composed of Grignard ACA to alkynyl enones.
Scheme 20: Rh/Cu-catalyzed tandem reaction of diazo enoates leading to cyclobutanes.
Scheme 21: Tandem Grignard-ACA of cyclopentenones and alkylation of enolates.
Scheme 22: Tandem ACA of Grignard reagents followed by enolate trapping reaction with onium compounds.
Scheme 23: Mg enolates generated from unsaturated lactones in reaction with activated alkenes.
Scheme 24: Lewis acid mediated ACA to amides and SN2 cyclization of a Br-appended enolate.
Scheme 25: Trapping reactions of aza-enolates with Michael acceptors.
Scheme 26: Si enolates generated by TMSOTf-mediated ACA of Grignard reagents and enolate trapping reaction wit...
Scheme 27: Trapping reactions of enolates generated from alkenyl heterocycles (A) and carboxylic acids (B) wit...
Scheme 28: Reactions of heterocyclic Mg enolates with onium compounds.
Scheme 29: Synthetic transformations of cycloheptatrienyl and benzodithiolyl substituents.
Scheme 30: Aminomethylation of Al enolates generated by ACA of trialkylaluminum reagents.
Scheme 31: Trapping reactions of enolates with activated alkenes.
Scheme 32: Alkynylation of racemic aluminum or magnesium enolates.
Scheme 33: Trapping reactions of Zr enolates generated by Cu-ACA of organozirconium reagents.
Scheme 34: Chloromethylation of Zr enolates using the Vilsmeier–Haack reagent.
Scheme 35: Tandem conjugate borylation with subsequent protonation or enolate trapping by an electrophile.
Scheme 36: Tandem conjugate borylation/aldol reaction of cyclohexenones.
Scheme 37: Selected examples for the tandem asymmetric borylation/intramolecular aldol reaction; synthesis of ...
Scheme 38: Cu-catalyzed tandem methylborylation of α,β-unsaturated phosphine oxide in the presence of (R,Sp)-J...
Scheme 39: Cu-catalyzed tandem transannular conjugated borylation/aldol cyclization of macrocycles containing ...
Scheme 40: Stereoselective tandem conjugate borylation/Mannich cyclization: selected examples (A) and a multi-...
Scheme 41: Some examples of Cu-catalyzed asymmetric tandem borylation/aldol cyclization (A). Application to di...
Scheme 42: Atropisomeric P,N-ligands used in tandem conjugate borylation/aldol cyclization sequence.
Scheme 43: Selected examples for the enantioselective Cu-catalyzed borylation/intramolecular Michael addition ...
Scheme 44: Selected examples for the preparation of enantioenriched spiroindanes using a Cu-catalyzed tandem c...
Scheme 45: Enantioselective conjugate borylation of cyclobutene-1-carboxylic acid diphenylmethyl ester 175 wit...
Scheme 46: Cu-catalyzed enantioselective tandem conjugate silylation of α,β-unsaturated ketones with subsequen...
Scheme 47: Cu-catalyzed enantioselective tandem conjugate silylation of α,β-unsaturated ketones with subsequen...
Scheme 48: Cu-catalyzed tandem conjugate silylation/aldol condensation. The diastereoselectivity is controlled...
Scheme 49: Chiral Ru-catalyzed three-component coupling reaction.
Scheme 50: Rh-Phebox complex-catalyzed reductive cyclization and subsequent reaction with Michael acceptors th...
Scheme 51: Rh-catalyzed tandem asymmetric conjugate alkynylation/aldol reaction (A) and subsequent spiro-cycli...
Scheme 52: Rh-bod complex-catalyzed tandem asymmetric conjugate arylation/intramolecular aldol addition (A). S...
Scheme 53: Co-catalyzed C–H-bond activation/asymmetric conjugate addition/aldol reaction.
Scheme 54: (Diisopinocampheyl)borane-promoted 1,4-hydroboration of α,β-unsaturated morpholine carboxamides and...
Figure 2: Some examples of total syntheses that have been recently reviewed.
Scheme 55: Stereoselective synthesis of antimalarial prodrug (+)-artemisinin utilizing a tandem conjugate addi...
Scheme 56: Amphilectane and serrulatane diterpenoids: preparation of chiral starting material via asymmetric t...
Scheme 57: Various asymmetric syntheses of pleuromutilin and related compounds based on a tandem conjugate add...
Scheme 58: Total synthesis of glaucocalyxin A utilizing a tandem conjugate addition/acylation reaction sequenc...
Scheme 59: Installation of the exocyclic double bond using a tandem conjugate addition/aminomethylation sequen...
Scheme 60: Synthesis of the taxol core using a tandem conjugate addition/enolate trapping sequence with Vilsme...
Scheme 61: Synthesis of the tricyclic core of 12-epi-JBIR-23/24 utilizing a Rh-catalyzed asymmetric conjugate ...
Scheme 62: Total synthesis of (−)-peyssonoside A utilizing a Cu-catalyzed enantioselective tandem conjugate ad...
Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates
- Bastian Jakob,
- Nico Schneider,
- Luca Gengenbach and
- Georg Manolikakes
Beilstein J. Org. Chem. 2023, 19, 719–726, doi:10.3762/bjoc.19.52
Graphical Abstract
Figure 1: Biologically active molecules containing α-arylglycine motifs (highlighted in green and blue).
Scheme 1: The Petasis reaction – fundamental reactivities and recent developments.
Scheme 2: Observations from previous studies and mechanistic rationale.
Scheme 3: Initial experiments.
Scheme 4: Reaction scope – aryltrifluoroborates (yields and enantiomeric ratios in parentheses refer to our p...
Scheme 5: Synthesis of both enantiomers of arylglycine building block 18.
Asymmetric tandem conjugate addition and reaction with carbocations on acylimidazole Michael acceptors
- Brigita Mudráková,
- Renata Marcia de Figueiredo,
- Jean-Marc Campagne and
- Radovan Šebesta
Beilstein J. Org. Chem. 2023, 19, 881–888, doi:10.3762/bjoc.19.65
Graphical Abstract
Scheme 1: Concept of this work.
Scheme 2: Initial experiments for the trapping of the intermediate enolate Enl-1a with tropylium NTf2.
Scheme 3: The reaction scope.
Figure 1: Comparison of DFT-calculated and experimental ECD of (2R,3R)-4 and (2S,3R)-4.
Figure 2: DFT calculated (ωB97X-D4/def2-TZVPPD//PBEh-3c/def2-mSVP) HOMO energies and NBO charges for represen...
New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones
- Vladislav Yu. Shuvalov,
- Ekaterina Yu. Vlasova,
- Tatyana Yu. Zheleznova and
- Alexander S. Fisyuk
Beilstein J. Org. Chem. 2023, 19, 1155–1160, doi:10.3762/bjoc.19.83
Graphical Abstract
Figure 1: Biologically active 4-arylpyrazolo[3,4-b]pyridin-6-ones.
Scheme 1: Methods for the synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones.
Scheme 2: One-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones 4a–i, 9a, and 10a.
Figure 2: Normalized absorption and fluorescence spectra of solutions of compounds 4a–i, 9a, and 10a in EtOH.
Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins
- Chandra Sekhar Tekuri,
- Pargat Singh and
- Mahendra Nath
Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89
Graphical Abstract
Scheme 1: Synthesis of benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 3–16.
Figure 1: Plausible mechanism for the formation of copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins.
Scheme 2: Sequential synthesis of copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrin 3.
Figure 2: Electronic absorption spectra of copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 3–8 in CHCl...
Figure 3: Electronic absorption spectra of free-base benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 9–13 in CHCl...
Figure 4: Electronic absorption spectra of zinc(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 14–16 in CHCl...
Figure 5: (a) Emission spectra of free-base benzo[f]chromeno[2,3-h]quinoxalinoporphyrins 9–13 and (b) emissio...
Acetaldehyde in the Enders triple cascade reaction via acetaldehyde dimethyl acetal
- Alessandro Brusa,
- Debora Iapadre,
- Maria Edith Casacchia,
- Alessio Carioscia,
- Giuliana Giorgianni,
- Giandomenico Magagnano,
- Fabio Pesciaioli and
- Armando Carlone
Beilstein J. Org. Chem. 2023, 19, 1243–1250, doi:10.3762/bjoc.19.92
Graphical Abstract
Scheme 1: Original triple organocatalytic cascade reaction developed by Enders.
Figure 1: Approaches based on the original Enders cascade reaction to access trisubstituted cyclohexene carba...
Scheme 2: Acetaldehyde dimethyl acetal (6) as an acetaldehyde surrogate to effect a triple organocatalytic ca...
Figure 2: Scope of the cascade reaction using 6 as an acetaldehyde equivalent. Reaction conditions: 3 (0.5 mm...
Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence
- Nadia Ledermann,
- Alae-Eddine Moubsit and
- Thomas J. J. Müller
Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99
Graphical Abstract
Scheme 1: Consecutive alkynylation–cyclization–alkylation three-component synthesis and conception of a conse...
Scheme 2: Consecutive alkynylation–cyclization–iodination–alkylation four-component synthesis of trisubstitut...
Scheme 3: Consecutive double alkynylation–cyclization–iodination–alkylation pseudo-five-component synthesis o...
Scheme 4: Suzuki coupling of 3-iodoindole 5a with arylboronic acids 7 to give 1,2,3-trisubstituted indoles 8.
Figure 1: A: Absorption and emission spectra of 1-methyl-2-phenyl-3-(p-tolyl)-1H-indole (8b), recorded in dic...
One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives
- Hans-Ulrich Reissig and
- Fei Yu
Beilstein J. Org. Chem. 2023, 19, 1399–1407, doi:10.3762/bjoc.19.101
Graphical Abstract
Scheme 1: Earlier approaches to multivalent carbohydrate mimetics B, D or F based on enantiopure aminopyran a...
Scheme 2: Synthesis of model compound 3 under conventional conditions and as a one-pot process employing benz...
Scheme 3: One-pot reaction employing enantiopure alkynyl-substituted 1,2-oxazin-4-one derivative 6 leading to...
Scheme 4: One-pot reactions of dihalides 8 and 11 with sodium azide and alkyne 2 leading to symmetric divalen...
Scheme 5: One-pot reactions employing enantiopure alkynyl-substituted 1,2-oxazin-4-one derivative 6 leading t...
Scheme 6: One-pot reaction employing enantiopure alkynyl-substituted 1,2-oxazin-4-ol derivative 19 leading to...
Scheme 7: Reductive ring-openings of 1,2-oxazine derivatives 19 and 23 as simple model compounds by hydrogeno...
Scheme 8: Attempted reductive ring-openings of compound 21 by hydrogenolysis or by samarium diiodide leading ...
Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds
- Xiaofeng Zhang,
- Xiaoming Ma and
- Wei Zhang
Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123
Graphical Abstract
Figure 1: Classification of AMYs.
Scheme 1: Aminoester- and amino acid-based AMYs for single and double [3+2] cycloadditions.
Scheme 2: Formation of semi-stabilized AMYs B1 from pyrrolidines.
Scheme 3: Cyclic amine-based AMYs A3 and B1 for [3 + 2] cycloadditions.
Scheme 4: Proposed double cycloaddition reactions involving semi-stabilized AMYs.
Scheme 5: [3 + 2] Cycloaddition for the synthesis of trifluoromethylated pyrrolidines 9.
Figure 2: Biologically interesting pyrrolizidines.
Scheme 6: Double cycloadditions with glycine for the synthesis of products 10 (dr > 9:1).
Scheme 7: Double cycloadditions with α-substituted amino acids leading to products 11 (≈8.5:1 dr).
Scheme 8: Stereochemistry for the formation of products 10 or 11.
Scheme 9: One-pot and stepwise double cycloadditions. Conditions: i) MeCN (0.02 M), 90 °C, 6 h; ii) then AcOH...
Figure 3: Biologically interesting spirooxindole-pyrrolizidines.
Scheme 10: Double cycloadditions for the synthesis of bis[spirooxindole-pyrrolizidine]s.
Scheme 11: Mechanism for the diastereoselective synthesis of bis[spirooxindole-pyrrolizidine]s.
Scheme 12: Stepwise synthesis of triazolobenzodiazepine 21a.
Scheme 13: One-pot synthesis of triazolobenzodiazepines.
Figure 4: Bioactive triazolobenzodiazepine derivatives.
Scheme 14: One-pot synthesis of tetrahydropyrroloquinazolines.
Scheme 15: One-pot synthesis of tetrahydropyrrolobenzodiazepines.
Figure 5: Bioactive pyrroloquinazolines and pyrrolobenzodiazepines.
Scheme 16: Stepwise synthesis of pyrrolo[2,1-a]isoquinolines.
Figure 6: Bioactive pyrrolo[2,1-a]isoquinolines and hexahydropyrrolo[2,1-a]isoquinolines.
Figure 7: Bioactive tetrahydropyrrolothiazoles.
Scheme 17: Pseudo-four-component reaction for the synthesis of tetrahydropyrrolothiazoles 29 and 30 (>4:1 dr).
Scheme 18: One-pot two-step synthesis of spirooxindole-pyrrolothiazoles 31 (>4:1 dr).
