Synthesis of Tetrasubstituted Enamines through Borane-Catalyzed Hydrogenations DOI
Zijia Zhang, Xiangqing Feng, Haifeng Du

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(51), P. 9142 - 9146

Published: Dec. 19, 2023

This paper describes a B(C6F5)3-catalyzed hydrogenation of β-substituted α,β-unsaturated imines by using as low 0.2 mol % catalyst. A variety tetrasubstituted enamines were afforded in 95-99% yields. It provides an efficient and facile way without the need for column chromatography purification.

Language: Английский

Chiral Diene Ligands in Asymmetric Catalysis DOI
Yinhua Huang, Tamio Hayashi

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(18), P. 14346 - 14404

Published: Aug. 16, 2022

Asymmetric catalysis has emerged as a general and powerful approach for constructing chiral compounds in an enantioselective manner. Hence, developing novel ligands catalysts that can effectively induce asymmetry reactions is crucial modern chemical synthesis. Among such catalysts, dienes their metal complexes have received increased attention, great progress been made over the past two decades. This review provides comprehensive critical information on essential aspects of diene importance asymmetric catalysis. The literature covered ranges from August 2003 (when first effective ligand was reported) to October 2021. divided into parts. In part, are categorized according structures, preparation methods summarized. second applications transformations presented reaction types.

Language: Английский

Citations

101
Asymmetric catalysis with FLPs DOI Creative Commons
Xiangqing Feng, Wei Meng, Haifeng Du

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(24), P. 8580 - 8598

Published: Jan. 1, 2023

This review provides an overview of the important progress in FLP-catalyzed asymmetric reactions made over past 15 years, and both merits limitations FLP-catalysis have been highlighted.

Language: Английский

Citations

20
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

13
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

0
Enantioselective Synthesis of 2-Aryl-3,3-Disubstituted Indolines from 3H-Indoles via Deracemization DOI
Guangyu Cui, Zaiqi Han, Xiangqing Feng

et al.

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

Published: April 8, 2025

An enantioselective synthesis of 2-aryl 3,3-disubstituted 3H-indoles has been successfully developed via a deracemization process involving borane-catalyzed hydrogenation and chiral phosphoric-acid-catalyzed asymmetric transfer hydrogenation. A variety were effective substrates to afford the desired indolines in 86-95% yields with 45-92% ee's.

Language: Английский

Citations

0
Asymmetric Transfer Hydrogenation of 2-Substituted Quinoxalines with Regenerable Dihydrophenanthridine DOI
Zaiqi Han, Xiangqing Feng, Haifeng Du

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3666 - 3671

Published: Feb. 15, 2024

The asymmetric hydrogenation of quinoxalines represents one the most efficient approaches for synthesis optically active tetrahyroquinoxalines. In this paper, we demonstrate a metal-free transfer 2-substituted with regenerable dihydrophenanthridine under H2 using combination chiral phosphoric acid and achiral borane as catalysts. A wide range tetrahydroquinoxalines were produced in high yields ≤98% ee.

Language: Английский

Citations

2
Enantioselective applications of frustrated Lewis pairs in organic synthesis DOI Creative Commons
Michael G. Guerzoni, Ayan Dasgupta, Emma Richards

et al.

Chem Catalysis, Journal Year: 2022, Volume and Issue: 2(11), P. 2865 - 2875

Published: Sept. 29, 2022

Language: Английский

Citations

10
Stereoselective Hydrosilylation of 1,2‐Diketones Catalyzed by Chiral Frustrated Lewis Pairs DOI
Ting Liu, Wei Meng, Xiangqing Feng

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(5)

Published: Dec. 9, 2023

The asymmetric reduction of 1,2-diketones for the synthesis optically active 1,2-diols, especially 1,2-anti-diols, remains a formidable challenge. In this paper, we describe first highly stereoselective hydrosilylation unsymmetrical vicinal diketones with PhSiH

Language: Английский

Citations

3
Asymmetric Hydrogenation of Phenanthridines with Chiral Boranes DOI
Guangyu Cui, Xiangqing Feng, Haifeng Du

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(6), P. 631 - 635

Published: Nov. 21, 2023

Comprehensive Summary The asymmetric hydrogenation of N ‐heteroarenes provides an efficient method for the synthesis optically active cyclic secondary amines. In this paper, we described phenanthridines using a chiral mono‐alkene‐derived borane. A variety dihydrophenanthridines were furnished in high yields with up to 93% ee. current catalytic system was very sensitive steric hindrance phenanthridines. Bulky substituents at one phenyl group required obtain enantioselectivity. But large on carbon C=N bonds would diminish reactivity sharply.

Language: Английский

Citations

2
Progress in Photocatalytic Hydrosilylation DOI Open Access
Jun Liu, Jiajian Peng, Ying Bai

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(10), P. 3558 - 3558

Published: Jan. 1, 2023

Organosilicon products have become an indispensable part of our lives today.Catalytic hydrosilylation reaction is one the important methods for preparing organosilicon chemicals and materials.The research development inexpensive excellent catalysts received extensive attention.At present, on catalytic mainly focuses exploring properties new noble metal non-precious complexes.However, due to high cost metals low activity non-noble complexes, photocatalysis environmentally friendly safe method.Catalytic photocatalytic reactions much attention.In this paper, progress in recent years introduced.

Language: Английский

Citations

1