Cited by Asymmetric Hydrogenation of Polysubstituted Isoquinolines with Chiral Boranes

Borane-Catalyzed Enantioselective α-Alkylation of Unactivated 2-Alkylbenzoxazoles with Electron-Deficient Olefins DOI

Chongren Ai,

Lu Liu, Xiaochen Wang

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(35), P. 24663 - 24669

Published: Aug. 20, 2024

Chiral borane–catalyzed reactions have recently emerged as a powerful tool for the enantioselective production of chiral scaffolds. In this study, we demonstrated first time that bisborane catalyst can be used α-functionalization 2-alkylazaarenes; specifically, accomplished unprecedented highly α-alkylation unactivated 2-alkylbenzoxazoles with electron-deficient olefins. The strong Lewis acidity and steric bulk were essential to observed reactivity selectivity.

Language: Английский

Citations

Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines DOI

Jun‐Jie Tian,

Zhao‐Ying Yang,

Xin‐Shen Liang

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(42), P. 18452 - 18456

Published: July 8, 2020

Abstract Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro‐bicyclic bisboranes as catalysts HBpin an acidic amide reducing reagents, proceeds through a cascade process involving 1,4‐hydroboration followed by transfer hydrogenation dihydropyridine intermediate. retained double bond in products permits their conversion to natural other useful heterocyclic compounds simple transformations.

Language: Английский

Citations

Iridium Complex-Catalyzed Transfer Hydrogenation of N-Heteroarenes and Tentative Asymmetric Synthesis DOI

Lu Ouyang,

Yanping Xia,

Jianhua Liao

et al.

ACS Omega, Journal Year: 2021, Volume and Issue: 6(15), P. 10415 - 10427

Published: April 7, 2021

An iridium-catalyzed transfer hydrogenation of N-heteroarenes to access a series substituted 1,2,3,4-tetrahydroquinoline derivatives in excellent yields is disclosed. This transformation distinguished with water-soluble and air-stable iridium complexes as the catalyst, formic acid hydrogen source, mild reaction conditions, broad functional group compatibility. Most importantly, tentative chiral N,N-chelated Cp*Ir(III) complex-catalyzed enantioselective also presented, affording products good enantioselectivities.

Language: Английский

Citations

Asymmetric Reduction of Quinolines: A Competition between Enantioselective Transfer Hydrogenation and Racemic Borane Catalysis DOI

Bochao Gao,

Zaiqi Han, Wei Meng

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(5), P. 3335 - 3339

Published: Feb. 17, 2023

A chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of quinolines with regenerable dihydrophenanthridine derived by a borane-catalyzed phenanthridine under H2 has been successfully realized. Despite the competition racemic pathway, variety tetrahydroquinolines were furnished in high yields up to 91% ee.

Language: Английский

Citations

Asymmetric Hydrogenation of Polysubstituted Isoquinolines with Chiral Boranes DOI

Fei-Ran Zou,

Xiangqing Feng, Haifeng Du

et al.

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

Published: Feb. 26, 2025

This paper describes an asymmetric hydrogenation of 1,3-disubstituted isoquinolines catalyzed by chiral borane derived from alkene, giving the desired cis-products in high yields with up to 96% ee. In particular, challenging 1,3,4-trisubstituted could proceed smoothly afford corresponding products moderate ee's for first time.

Language: Английский

Citations