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

[21] Enantioselective Hydrosilylation of Imines Catalyzed by Diamine-Zinc Complexes [J].

Park, Bu-Mahn ;

Feng, Xinhui ;

Yun, Jaesook .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (08) :2960-2964

[22] Hydrosilylation of Aromatic Aldehydes and Ketones Catalyzed by Mono- and Tri-Nuclear Platinum(0) Complexes [J].

Tsuchido, Yoshitaka ;

Abe, Ryota ;

Kamono, Megumi ;

Tanaka, Kimiya ;

Tanabe, Makoto ;

Osakada, Kohtaro .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2018, 91 (05) :858-864

[23] Enantioselective Hydrosilylation of Ketones Catalyzed by a Readily Accessible N-Heterocyclic Carbene-Ir Complex at Room Temperature [J].

Shinohara, Kanako ;

Kawabata, Shun ;

Nakamura, Hanako ;

Manabe, Yoshiki ;

Sakaguchi, Satoshi .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (25) :5532-5539

[24] Enantioselective Zinc-Catalyzed Hydrosilylation of Ketones using Pybox or Pybim Ligands [J].

Junge, Kathrin ;

Moeller, Konstanze ;

Wendt, Bianca ;

Das, Shoubhik ;

Goerdes, Dirk ;

Thurow, Kerstin ;

Beller, Matthias .

CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (02) :314-320

[25] Enantioselective Direct Alkynylation of Ketones Catalyzed by Chiral CCN Pincer RhIII Complexes [J].

Ito, Jun-ichi ;

Ubukata, Shino ;

Muraoka, Shun ;

Nishiyama, Hisao .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (47) :16800-16803

[26] Copper(II)-catalyzed enantioselective hydrosilylation of halo-substituted alkyl aryl and heteroaryl ketones: asymmetric synthesis of (R)-fluoxetine and (S)-duloxetine [J].

Zhou, Ji-Ning ;

Fang, Qiang ;

Hu, Yi-Hu ;

Yang, Li-Yao ;

Wu, Fei-Fei ;

Xie, Lin-Jie ;

Wu, Jing ;

Li, Shijun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (06) :1009-1017

[27] Bis(oxazoline)titanium complexes as chiral catalysts for enantioselective hydrosilylation of ketones - A combined experimental and theoretical investigation [J].

Bandini, M ;

Bernardi, F ;

Bottoni, A ;

Cozzi, PG ;

Miscione, GP ;

Umani-Ronchi, A .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (15) :2972-2984

[28] Construction of a Chiral Silicon Center by Rhodium-Catalyzed Enantioselective Intramolecular Hydrosilylation [J].

Naganawa, Yuki ;

Namba, Tomoya ;

Kawagishi, Mayu ;

Nishiyama, Hisao .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (26) :9319-9322

[29] Enantioselective insertion of carbenoids into N-H bonds catalyzed by chiral bicyclobisoxazoline copper(I) complexes [J].

Le Maux, Paul ;

Simonneaux, Gerard .

TETRAHEDRON, 2015, 71 (49) :9333-9338

[30] Iminophenyl Oxazolinylphenylamine for Enantioselective Cobalt-Catalyzed Hydrosilylation of Aryl Ketones [J].

Chen, Xu ;

Lu, Zhan .

ORGANIC LETTERS, 2016, 18 (18) :4658-4661

← 1 2 3 4 5 →