Enantioselective hydrosilylation of prochiral ketones catalyzed by chiral BINAP-copper(I) complexes

被引：11

作者：

Issenhuth, Jean-Thomas ^{[1
]}

Dagorne, Samuel ^{[1
]}

Bellemin-Laponnaz, Stephane ^{[1
]}

机构：

[1] Univ Strasbourg, Inst Chim, CNRS, F-67000 Strasbourg, France

来源：

COMPTES RENDUS CHIMIE | 2010年 / 13卷 / 03期

关键词：

Asymmetric catalysis; Hydrosilylation; Copper; Hydride; ASYMMETRIC HYDROSILYLATION; COPPER; RHODIUM; REDUCTION; CARBONYL; LIGANDS; ALKYL; CYCLOPENTANONES; AIR;

D O I：

10.1016/j.crci.2009.11.002

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The CuCl/NaOt-Bu/BINAP system was found to efficiently catalyze the hydrosilylation of aryl alkyl ketones with excellent enantioselectivities by using phenyl methyl silane as a stoichiometric hydride source. High enantiomeric excesses (up to 97%) and excellent yields (up to 99%) were obtained. (C) 2009 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.

引用

页码：353 / 357

页数：5

共 50 条

[31] Enantioselective Hydrosilylation of Aromatic Alkenes Catalyzed by Chiral Bis(oxazolinyl)phenyl-Rhodium Acetate Complexes [J].

Naito, Tatsuo ;

Yoneda, Takuma ;

Ito, Jun-ichi ;

Nishiyama, Hisao .

SYNLETT, 2012, (20) :2957-2960

[32] Rh-catalyzed enantioselective hydrosilylation of aromatic ketones using (S,S)-Phos-Biox as a chiral ligand [J].

Lee, S ;

Lim, CW .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2001, 22 (02) :231-233

[33] Selective hydrosilylation of ketones catalyzed by in situ-generated iron NHC complexes [J].

Buitrago, Elina ;

Zani, Lorenzo ;

Adolfsson, Hans .

APPLIED ORGANOMETALLIC CHEMISTRY, 2011, 25 (10) :748-752

[34] Zinc-Catalyzed Enantioselective Hydrosilylation of Ketones and Imines under Solvent-Free Conditions [J].

Szewczyk, Marcin ;

Bezlada, Agata ;

Mlynarski, Jacek .

CHEMCATCHEM, 2016, 8 (23) :3575-3579

[35] Enantioselective Synthesis of α-Hydroxy Allyl Ketones via BINAP-CuH-Catalyzed Hydroacylation [J].

Maurya, Sundaram ;

Navaneetha, N. ;

Behera, Prativa ;

Nanubolu, Jagadeesh Babu ;

Roy, Lisa ;

Chegondi, Rambabu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (15)

[36] Hydrosilylation of Aldehydes and Ketones Catalyzed by HalfSandwich Manganese( I) N-Heterocyclic Carbene Complexes [J].

Zheng, Jianxia ;

Elangovan, Saravanakumar ;

Valyaev, Dmitry A. ;

Brousses, Remy ;

Cesar, Vincent ;

Sortais, Jean-Baptiste ;

Darcel, Christophe ;

Lugan, Noel ;

Lavigne, Guy .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (05) :1093-1097

[37] Asymmetric Hydrosilylation of Aromatic Ketones Catalyzed by an Economical and Effective Copper-Diphosphine Catalytic System in Air [J].

Liang, Minting ;

Xia, Xiaofeng ;

Liu, Xiang ;

Li, Hexing .

CHINESE JOURNAL OF CHEMISTRY, 2015, 33 (05) :578-582

[38] First application of chiral phosphotriesters in asymmetric metal catalysis: enantioselective Zn-catalyzed hydrosilylation of ketones in the presence of BINOL-derived phosphates [J].

Ndimba, Alphonsine Ngo ;

Roisnel, Thierry ;

Argouarch, Gilles ;

Lalli, Claudia .

COMPTES RENDUS CHIMIE, 2021, 24 (02) :77-81

[39] CuII-Catalyzed Asymmetric Hydrosilylation of Diaryl- and Aryl Heteroaryl Ketones: Application in the Enantioselective Synthesis of Orphenadrine and Neobenodine [J].

Sui, Yao-Zong ;

Zhang, Xi-Chang ;

Wu, Jun-Wen ;

Li, Shijun ;

Zhou, Ji-Ning ;

Li, Min ;

Fang, Wenjun ;

Chan, Albert S. C. ;

Wu, Jing .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (24) :7486-7492

[40] Enantioselective copper(II)-catalyzed Henry reaction utilizing chiral aziridinyl alcohols [J].

Wang, Xiaojuan ;

Zhao, Wenxian ;

Li, Gaowei ;

Wang, Jin ;

Liu, Guanjun ;

Liu, Lantao ;

Zhao, Ruijuan ;

Wang, Mincan .

APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (12) :892-899

← 1 2 3 4 5 →