Recent Advances in the Synthesis of Chiral Tetrahydroisoquinolines via Asymmetric Reduction DOI Open Access
Yue Ji, Qiang Gao, Weiwei Han

et al.

Catalysts, Journal Year: 2024, Volume and Issue: 14(12), P. 884 - 884

Published: Dec. 3, 2024

Enantiopure tetrahydroisoquinolines (THIQs), recognized as privileged skeletal structures in natural alkaloids, have attracted considerable attention from chemists due to their biological and pharmacological activities. Synthetic strategies for optically active THIQs been rapidly extensively developed the past decades. In view of simplicity atom economy, asymmetric reduction N-heteroaromatics, imines, enamines, iminium salts containing an isoquinoline (IQ) moiety should be preferred approaches obtain chiral THIQs. This review focuses on recent advances catalytic synthesis enantiopure via reduction, including hydrogenation, transfer reductive amination, deracemization. Highly enantioselective was achieved transition-metal-catalyzed organocatalytic utilizing either catalyst activation or substrate strategy. Despite much progress THIQs, there still remain opportunities challenges developments this field research, particularly development systems direct IQs.

Language: Английский

Photochemical Deracemization of Lactams with Deuteration Enabled by Dual Hydrogen Atom Transfer DOI
Xiaoyu Yan,

Yubing Pang,

Yutong Zhou

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

Photochemical deracemization has emerged as one of the most straightforward approaches to access highly enantioenriched compounds in recent years. While excited-state events such energy transfer, single electron and ligand-to-metal charge transfer have been leveraged promote stereoablation, relying on hydrogen atom which circumvent limitations imposed by triplet redox potential racemic substrates, remain underexplored. Conceptually, attractive method for tertiary stereocenter might be abstraction followed donation. However, implementing a strategy poses significant challenges, primarily because products are also reactive if chiral catalyst is unable differentiate between two enantiomers. Herein we report distinct dual photochemical δ- γ-lactams, achieving high enantioenrichment deuterium incorporation despite inherent reactivity products. Mechanistic studies reveal that benzophenone enables nonselective while tetrapeptide-derived thiol dictates enantioselectivity donation step. More importantly, pyridine-based alcohol was found play crucial roles facilitating well enhancing

Language: Английский

Citations

5
Visible Light-Promoted Deracemization of α-Amino Aldehyde by Synergistic Chiral Primary Amine and Hypervalent Iodine Catalysis DOI
Tianrun Pan,

Xieyang Jiang,

Mouxin Huang

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 6, 2025

α-Amino aldehydes, as versatile chiral synthons, are easily racemized under normal acid or base conditions, seriously limiting their synthetic potentials. We report herein an effective deracemization of α-amino aldehydes by a synergistic primary amine and hypervalent iodine catalysis visible light. The developed catalytic system allows for the on-demand production α-Boc- Cbz-protected amino with high enantioselectivity. Mechanistic studies verified photochemical Z-E isomerization mechanism that drives process.

Language: Английский

Citations

0
(S)-Convergent Deracemization of Racemic Esters with (R)-Selective Lipase: Pickering Emulsion Strategy for Enantiodivergent Synthesis Using a Native Enzyme DOI

Tomoya Nishio,

Shuji Akai, Kyohei Kanomata

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6565 - 6571

Published: April 7, 2025

Language: Английский

Citations

0
Recent Advances in the Synthesis of Chiral Tetrahydroisoquinolines via Asymmetric Reduction DOI Open Access
Yue Ji, Qiang Gao, Weiwei Han

et al.

Catalysts, Journal Year: 2024, Volume and Issue: 14(12), P. 884 - 884

Published: Dec. 3, 2024

Enantiopure tetrahydroisoquinolines (THIQs), recognized as privileged skeletal structures in natural alkaloids, have attracted considerable attention from chemists due to their biological and pharmacological activities. Synthetic strategies for optically active THIQs been rapidly extensively developed the past decades. In view of simplicity atom economy, asymmetric reduction N-heteroaromatics, imines, enamines, iminium salts containing an isoquinoline (IQ) moiety should be preferred approaches obtain chiral THIQs. This review focuses on recent advances catalytic synthesis enantiopure via reduction, including hydrogenation, transfer reductive amination, deracemization. Highly enantioselective was achieved transition-metal-catalyzed organocatalytic utilizing either catalyst activation or substrate strategy. Despite much progress THIQs, there still remain opportunities challenges developments this field research, particularly development systems direct IQs.

Language: Английский

Citations

1