Enantioselective Cascade Annulation of 1,2,3-Triazoles and Enals Enabled by Sequential Rhodium and Oxidative NHC Catalysis Involving Cleavage, Migration, and Cyclization DOI

Xiaoyi Yu,

Hao An, Wenbin Wu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

The in situ-generated pyrrolin-3-ones serve as novel and versatile synthons, being employed intermediates for the efficient production of pyrrole-fused lactones with high yield excellent enantioselectivity. Herein, we introduce emerging rhodium oxidative N-heterocyclic carbene relay catalysis that enables a highly enantioselective cascade annulation between easily available 1,2,3-triazoles enals. In this proof-of-concept study, engage α,β-unsaturated acylazolium generated from enals via catalysis.

Language: Английский

Enantioselective synthesis of molecules with multiple stereogenic elements DOI Creative Commons
Arthur Gaucherand, Expédite Yen‐Pon,

Antoine Domain

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(22), P. 11165 - 11206

Published: Jan. 1, 2024

This review explores the fascinating world of molecules featuring multiple stereogenic elements, unraveling different strategies designed over years for their enantioselective synthesis.

Language: Английский

Citations

12
Asymmetric Organocatalytic 1,6-Conjugate Addition of Alkynyl 8-Methylenenaphthalen-2(8H)-one Formed In Situ: Synergistic Construction of Axial and Central Chirality DOI

Meiwen Liu,

Yihao Zhang,

Xin-Yan Ke

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 26, 2025

Organocatalytic enantioselective formal nucleophilic substitution reactions of α-(2-hydroxynaphthalen-8-yl)propargyl alcohols with 1-(1H-indol-3-yl)naphthalen-2-ols have been established for the first time. With aid a suitable chiral phosphoric acid, alkynyl 8-methylenenaphthalen-2(8H)-one was formed in situ from corresponding alcohol, followed by 1,6-conjugate additions to afford number enantioenriched (Ra,Sc)-2,3-disubstituted indoles 50-80% yields 81-93% ee and (Sa,Sc)-2,3-disubstituted 18-40% 79-96% ee. Notably, these products were characterized presence functional groups, including indole, naphthol, units, while exhibiting both axial central chirality.

Language: Английский

Citations

0
Atroposelective [4+1] Annulation for the Synthesis of Isotopic Isoindolinones Bearing both Central and Axial Chirality DOI Creative Commons

Jun Gu,

Lihong Zhang,

Hongfeng Zhuang

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Isotopically chiral molecules have drawn much attention due to their practical applications in drug discovery. However, existing studies this area are mainly limited centrally and H/D exchange. Herein, we report a phosphoric acid-catalyzed atroposelective [4+1] annulation of ketoaldehydes 1H-indol-1-amines. By means strategy, series D- 18O-labeled atropisomers featuring both central axial chiralities synthesized with high enantioselectivities diastereoselectivities good excellent isotopic incorporation. Experimental density functional theory suggest that the reaction involves sequential condensation, cyclization isomerization cascade, which second step is enantio-determining process.

Language: Английский

Citations

0
Enantioselective Cascade Annulation of 1,2,3-Triazoles and Enals Enabled by Sequential Rhodium and Oxidative NHC Catalysis Involving Cleavage, Migration, and Cyclization DOI

Xiaoyi Yu,

Hao An, Wenbin Wu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

The in situ-generated pyrrolin-3-ones serve as novel and versatile synthons, being employed intermediates for the efficient production of pyrrole-fused lactones with high yield excellent enantioselectivity. Herein, we introduce emerging rhodium oxidative N-heterocyclic carbene relay catalysis that enables a highly enantioselective cascade annulation between easily available 1,2,3-triazoles enals. In this proof-of-concept study, engage α,β-unsaturated acylazolium generated from enals via catalysis.

Language: Английский

Citations

0