From gem‐Dichlorocyclobutenones to Cyclobutenols: Unveiling a Ruthenium‐Catalyzed Allylic Reduction‐Asymmetric Transfer Hydrogenation Cascade DOI
Christophe Meyer,

Olivier Charron,

Marharyta Kosiuha

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 28, 2024

Abstract Cyclobutenones constitute an appealing class of substrates in catalytic asymmetric transformations leading to diversely substituted enantioenriched four‐membered carbocycles, which are eliciting a growing interest medicinal chemistry. Whilst several synthetically useful enantioselective conjugate addition reactions have been reported, the reduction carbonyl group simple cyclobutenones remains elusive transformation. Herein, we disclose discovery novel allylic reduction‐asymmetric transfer hydrogenation cascade, catalyzed by Noyori‐Ikariya ruthenium complex, from readily available gem ‐dichlorocyclobutenones, 2‐chlorocyclobutenols with high optical purities, can be engaged postfunctionalization enabling access rings.

Language: Английский

Synthesis of Chiral Heterocycles Through Enantioselective Silver‐Catalyzed Transformations DOI Open Access

Hélène Pellissier

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

Abstract This review collects the recent developments in synthesis of chiral heterocycles through enantioselective silver‐catalyzed transformations published since 2018. It demonstrates power silver catalysts as special mild Lewis acids to provide an impressive diversity reaction pathways, such 1,3‐dipolar cycloadditions, various types cyclizations, along with a wide variety more complex domino/tandem reactions, allowing many novel heterocyclic products be achieved high enantioselectivities.

Language: Английский

Citations

1
Recent Developments in Enantioselective Silver-Catalyzed Transformations DOI

Hélène Pellissier

Organic Preparations and Procedures International, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 95

Published: April 11, 2025

Language: Английский

Citations

0
Synthesis of Substituted Tetralins via Nitrogen Deletion/Diels–Alder Cascade Reaction DOI Creative Commons
Zixuan Zang,

Wen Ye,

Ka-leung Cheng

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 21, 2024

Skeletal editing is an important approach for the modification and diversification of biologically active molecules. The utilization nitrogen deletion strategies in skeletal has recently emerged as a new method compound modification. Here, we report unexpected isoindolines. Contrary to anticipated outcome cyclobutane formation via intramolecular radical couplings, isoindoline triggers Diels–Alder cycloaddition facilitated by situ ortho-xylylene yield tetraline. Inspired this reaction, developed strategy synthesizing substituted tetralins, employing isoindoline, reagent (anomeric amide), dienophiles. This methodology demonstrates pathway tetralin synthesis

Language: Английский

Citations

1
Synthesis of polysubstituted fused pyrrolidines via [2 + 2]/[2 + 3] cycloaddition of azomethine ylides DOI

Chunyan Ou,

Jian Wang,

Pingping Yin

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4149 - 4155

Published: Jan. 1, 2024

A general approach via [2 + 2]/[2 3] cycloaddition is elaborated for the preparation of densely substituted 3-azabicyclo[3.2.0]heptanes in good yields with excellent diastereoselectivities.

Language: Английский

Citations

0
Copper-Catalyzed Asymmetric [3 + 2] Cycloaddition of N-2,2,2-Trifluoroethylisatin Ketimines to Access Three Classes of Polyfunctionalized Spiro-Pyrrolidine–Oxindole Motifs DOI

Wenfeng Xu,

Ren-Xu Xiao,

Shuo Lv

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7376 - 7381

Published: Aug. 22, 2024

A facile copper-catalyzed [3 + 2] cycloaddition of N-2,2,2-trifluoroethylisatin ketimines with various electron-deficient alkenes to access structurally polyfunctionalized spiro-pyrrolidine–oxindole motifs has been developed. Under the catalytic system, could be utilized react a series exocyclic alkenes, including 2-acylamino acrylates, 3-methylene-β-lactams, and sterically hindered cycloalkenes represented by cyclobutenone, obtain variety densely functionalized spiro-pyrrolidine frameworks bearing an α-amino acid ester, β-lactam, cyclobutanone, respectively, in generally good yields excellent diastereo- enantioselectivities.

Language: Английский

Citations

0
From gem‐Dichlorocyclobutenones to Cyclobutenols: Unveiling a Ruthenium‐Catalyzed Allylic Reduction‐Asymmetric Transfer Hydrogenation Cascade DOI
Christophe Meyer,

Olivier Charron,

Marharyta Kosiuha

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 28, 2024

Abstract Cyclobutenones constitute an appealing class of substrates in catalytic asymmetric transformations leading to diversely substituted enantioenriched four‐membered carbocycles, which are eliciting a growing interest medicinal chemistry. Whilst several synthetically useful enantioselective conjugate addition reactions have been reported, the reduction carbonyl group simple cyclobutenones remains elusive transformation. Herein, we disclose discovery novel allylic reduction‐asymmetric transfer hydrogenation cascade, catalyzed by Noyori‐Ikariya ruthenium complex, from readily available gem ‐dichlorocyclobutenones, 2‐chlorocyclobutenols with high optical purities, can be engaged postfunctionalization enabling access rings.

Language: Английский

Citations

0