Highly Efficient and Enantioselective Iridium-Catalyzed Asymmetric Reductive Cycloetherification DOI
Yan Zong,

Xiaomei Zou,

Hongqi Tao

et al.

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

Published: Nov. 25, 2024

A catalytic protocol for the iridium-catalyzed asymmetric hydrogenation (AH) of γ- or δ-hydroxy ketones to rapidly assemble various aliphatic enantioenriched tetrahydrofurans (THFs) tetrahydropyrans (THPs) is disclosed. wide range THFs THPs were obtained in high yields and excellent enantioselectivities (up 99% up 96.5:3.5 er). The dynamic kinetic resolution (DKR-AH) process was also achieved, simultaneously constructing THP scaffolds with two contiguous stereogenic centers stereoselectivities 92% yield, 98.5:1.5 er >20:1 dr). Mechanistic investigation indicates that key step reaction involves AH challenging cyclic, oxocarbenium ions. Furthermore, this enantioselective approach could be carried out on a gram scale, cyclic ethers further transformed into an array useful building blocks natural products bioactive molecules.

Language: Английский

Selectfluor-mediated oxidative deamination: A scalable approach to aromatic aldehydes synthesis DOI
Chao Gao, Lin Li, Xiangyang Lin

et al.

Synthetic Communications, Journal Year: 2025, Volume and Issue: 55(5), P. 433 - 441

Published: Jan. 30, 2025

The catalyst-free oxidative deamination without over-oxidation constitutes a considerable challenge in the synthesis of aromatic aldehydes. Herein, we introduce Selectfluor-mediated Lewis acid system that achieves benzylic amines with α-C-H bond activation to yield Noteworthy features include direct use Selectfluor can activate under catalyst- and base-free conditions via in-situ dehydrofluorination effect. approach is demonstrated for broad scope accomplishes 200 mmol scale synthesis.

Language: Английский

Citations

0
Boron Compounds as Key Drivers of Innovation: Exploring Their Role in Environmental Remediation, Sustainable Agriculture, Advanced Biomedical Applications, and Green Chemistry DOI
Metin Yıldırım, Mehmet Erşatır, Mohammed Saleh

et al.

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: 1035, P. 123688 - 123688

Published: April 28, 2025

Language: Английский

Citations

0
Hydride Shuttle Catalysis: From Conventional to Inverse Mode DOI Creative Commons
Iakovos Saridakis, Immo Klose, Benjamin T. Jones

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(9), P. 3358 - 3369

Published: Aug. 19, 2024

Hydride shuttle catalysis has emerged as a powerful synthetic platform, enabling the selective formation of C–C bonds to yield sp3-rich structures. By virtue compelling reactivity sterically encumbered Lewis acids from frustrated pair regime, hydride enables regioselective functionalization alkyl amines at either α- or β-position. In contrast classical acid reactivity, increased steric hindrance prevents interaction with basic amine itself, instead leading reversible abstraction α-carbon. The created positive charge facilitates occurrence transformations before rebound similar capture event happen. this Perspective, we outline broad selection featuring catalysis, well recently developed approach inverse catalysis. Both strategies give rise wide array functionalized and offer elegant approaches otherwise elusive bond formations.

Language: Английский

Citations

1
Highly Efficient and Enantioselective Iridium-Catalyzed Asymmetric Reductive Cycloetherification DOI
Yan Zong,

Xiaomei Zou,

Hongqi Tao

et al.

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

Published: Nov. 25, 2024

A catalytic protocol for the iridium-catalyzed asymmetric hydrogenation (AH) of γ- or δ-hydroxy ketones to rapidly assemble various aliphatic enantioenriched tetrahydrofurans (THFs) tetrahydropyrans (THPs) is disclosed. wide range THFs THPs were obtained in high yields and excellent enantioselectivities (up 99% up 96.5:3.5 er). The dynamic kinetic resolution (DKR-AH) process was also achieved, simultaneously constructing THP scaffolds with two contiguous stereogenic centers stereoselectivities 92% yield, 98.5:1.5 er >20:1 dr). Mechanistic investigation indicates that key step reaction involves AH challenging cyclic, oxocarbenium ions. Furthermore, this enantioselective approach could be carried out on a gram scale, cyclic ethers further transformed into an array useful building blocks natural products bioactive molecules.

Language: Английский

Citations

1