Catalytic Atroposelective Synthesis of C−N Axially Chiral Aminophosphines via Dynamic Kinetic Resolution DOI Creative Commons
Carlos Rodríguez-Franco, Esther Roldán‐Molina, Alberto Aguirre‐Medina

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(37)

Published: June 25, 2024

Abstract A ruthenium‐catalyzed reductive amination via asymmetric transfer hydrogenation (ATH) has been used to perform an efficient dynamic kinetic resolution (DKR) of N ‐aryl 2‐formyl pyrroles decorated with a phosphine moiety positioned at the ortho’ position. The strategy relies on labilization stereogenic axis in substrate facilitated by transient Lewis acid‐base interaction (LABI) between carbonyl carbon and phosphorus center. reaction features broad scope aliphatic amines pyrrole scaffolds, proceeds under very mild conditions afford P , atropisomers good high yields excellent enantioselectivities (up 99 % ee ) for both diphenyl dicyclohexylphosphino derivatives.

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

17
Dynamic kinetic resolution and dynamic kinetic asymmetric transformation of atropisomeric biaryls DOI
Jie Zhang,

Xuan-Zhu Huo,

Yidan Liu

et al.

Chem Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 101329 - 101329

Published: March 1, 2025

Language: Английский

Citations

1
Development of Configurationally Labile Biaryl Reagents for Atropisomer Synthesis DOI
Changhui Wu, Jin Yang, Xiaoyuan Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(28)

Published: May 16, 2024

Abstract Axially chiral biaryl scaffolds are important in pharmaceuticals, natural products, and asymmetric synthesis. Atroposelective ring‐opening of configurationally labile reagents via dynamic kinetic transformation provides a valuable approach to access axially atropisomers. This review summarizes seminal contributions recent advancements on this topic based the use different types reagents.

Language: Английский

Citations

6
Palladium-catalyzed coupling of aryl sulfonium salts with [TBA][P(SiCl3)2] for the construction of tertiary phosphines DOI

Yao Chai,

Yaling Tian,

Jinhong Jia

et al.

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

Published: Jan. 1, 2025

We present a strategy for the synthesis of triarylphosphines via palladium-catalyzed C–P cross-coupling reactions aryl sulfonium salts with [TBA][P(SiCl 3 ) 2 ].

Language: Английский

Citations

0
Manual Grinding and Sunlight Synergistically Promoted Sulfonylation of Alkenyl Sulfonium Salts with Sulfinic Acids DOI
Lihua Yang, Lin Chen, Weijun Yao

et al.

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

Published: April 10, 2025

An environmentally friendly and practical method for the synthesis of various vinyl sulfones was developed through direct sulfonylation alkenyl sulfonium salts with sulfinic acids. The reaction effectively triggered by combined actions milling, sunlight, photocatalysts under solvent-free conditions, offering advantages such as a short time (5-10 min), room temperature, straightforward workup procedure. Preliminary mechanistic studies suggested that sulfonyl radical may be involved in this mechanophotocatalytic transformation process.

Language: Английский

Citations

0
Modular Assembly of Axially Chiral QUINAP Derivatives via Nickel-Catalyzed Enantioselective C–P Cross-Coupling DOI
Zhiping Yang,

Xiaodong Gu,

Li‐Biao Han

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 8268 - 8273

Published: May 2, 2025

Language: Английский

Citations

0
Catalytic Atroposelective Synthesis of C−N Axially Chiral Aminophosphines via Dynamic Kinetic Resolution DOI
Carlos Rodríguez-Franco, Esther Roldán‐Molina, Alberto Aguirre‐Medina

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(37)

Published: June 25, 2024

A ruthenium-catalyzed reductive amination via asymmetric transfer hydrogenation (ATH) has been used to perform an efficient dynamic kinetic resolution (DKR) of N-aryl 2-formyl pyrroles decorated with a phosphine moiety positioned at the ortho' position. The strategy relies on labilization stereogenic axis in substrate facilitated by transient Lewis acid-base interaction (LABI) between carbonyl carbon and phosphorus center. reaction features broad scope aliphatic amines pyrrole scaffolds, proceeds under very mild conditions afford P,N atropisomers good high yields excellent enantioselectivities (up 99 % ee) for both diphenyl dicyclohexylphosphino derivatives.

Language: Английский

Citations

2
Cu-Promoted Divergent Phosphination of Alkynylsulfonium Salts with Diarylphosphines DOI

Jinghui Sun,

Hao Tong,

Yifei Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7414 - 7418

Published: Aug. 27, 2024

An efficient copper-promoted divergent phosphination of alkynylsulfonium salts 1 with secondary diarylphosphines 2 that tolerates a wide range functional groups under mild conditions is reported. The use excess alkynyl dibenzothiophenium (1/2 > 1, mole ratio) enables the to deliver monophosphine products via C(sp)–P cross-coupling in good high yields, while < 0.5, leads type cis-ethenyl bisphosphine sequential stereoselective double phosphination.

Language: Английский

Citations

1
Catalytic Atroposelective Synthesis of C−N Axially Chiral Aminophosphines via Dynamic Kinetic Resolution DOI Creative Commons
Carlos Rodríguez-Franco, Esther Roldán‐Molina, Alberto Aguirre‐Medina

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(37)

Published: June 25, 2024

Abstract A ruthenium‐catalyzed reductive amination via asymmetric transfer hydrogenation (ATH) has been used to perform an efficient dynamic kinetic resolution (DKR) of N ‐aryl 2‐formyl pyrroles decorated with a phosphine moiety positioned at the ortho’ position. The strategy relies on labilization stereogenic axis in substrate facilitated by transient Lewis acid‐base interaction (LABI) between carbonyl carbon and phosphorus center. reaction features broad scope aliphatic amines pyrrole scaffolds, proceeds under very mild conditions afford P , atropisomers good high yields excellent enantioselectivities (up 99 % ee ) for both diphenyl dicyclohexylphosphino derivatives.

Language: Английский

Citations

0