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

[41] Enantioselective Hydrogenation of Ketones Catalyzed by Chiral Cobalt Complexes Containing PNNP Ligand [J].

Zhang, Dong ;

Zhu, En-Ze ;

Lin, Zhi-Wei ;

Wei, Zan-Bin ;

Li, Yan-Yun ;

Gao, Jing-Xing .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (11) :1323-1326

[42] Enantioselective Synthesis of exo-4-Nitroprolinates from Nitroalkenes and Azomethine Ylides Catalyzed by Chiral Phosphoramidite•Silver(I) or Copper(II) Complexes [J].

Castello, Luis M. ;

Najera, Carmen ;

Sansano, Jose M. ;

Larranaga, Olatz ;

de Cozar, Abel ;

Cossio, Fernando P. .

SYNTHESIS-STUTTGART, 2015, 47 (07) :934-943

[43] Enantioselective Copper-Catalyzed Sequential Hydrosilylation of Arylmethylenecyclopropanes [J].

Fu, Bin ;

Wang, Lianghua ;

Chen, Kexin ;

Yuan, Xiuping ;

Yin, Jianjun ;

Wang, Simin ;

Shi, Dazhen ;

Zhu, Bo ;

Guan, Wei ;

Zhang, Qian ;

Xiong, Tao .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (42)

[44] Asymmetric Synthesis of Trisubstituted Vicinal Diols through Copper(I)-Catalyzed Diastereoselective and Enantioselective Allylation of Ketones with Siloxypropadienes [J].

Jiang, Nan ;

Liu, Pei-Zhi ;

Pan, Zhi-Zhou ;

Wang, Si-Qing ;

Peng, Qian ;

Yin, Liang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (21)

[45] Hydrosilylation of Ketones Catalyzed by Iron Iminobipyridine Complexes and Accelerated by Lewis Bases [J].

Kobayashi, Katsuaki ;

Izumori, Yosuke ;

Taguchi, Daisuke ;

Nakazawa, Hiroshi .

CHEMPLUSCHEM, 2019, 84 (08) :1094-1102

[46] Highly asymmetric Henry reaction catalyzed by chiral copper(II) complexes [J].

Ni, Bukuo ;

He, Junpeng .

TETRAHEDRON LETTERS, 2013, 54 (06) :462-465

[47] Enantioselective nitroaldol reaction catalyzed by chiral C1-tetrahydro-1,1′-bisisoquinoline-copper(I) complexes [J].

Ji, Yao Qiong ;

Qi, Gao ;

Judeh, Zaher M. A. .

TETRAHEDRON-ASYMMETRY, 2011, 22 (09) :929-935

[48] Asymmetric Hydrosilylation of Ketones Catalyzed by Magnetically Recoverable and Reusable Copper Ferrite Nanoparticles [J].

Kantam, M. Lakshmi ;

Yadav, Jagjit ;

Laha, Soumi ;

Srinivas, Pottabathula ;

Sreedhar, Bojja ;

Figueras, F. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (12) :4608-4611

[49] Highly enantioselective hydrosilylation/cyclization of 1,6-enynes catalyzed by rhodium(I) complexes of spiro diphosphines [J].

Fan, Bao-Min ;

Xie, Jian-Hua ;

Li, Shen ;

Wang, Li-Xin ;

Zhou, Qi-Lin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (08) :1275-1277

[50] Hydrosilylation of alkenes and ketones catalyzed by nickel(II) indenyl complexes [J].

Fontaine, FG ;

Nguyen, RV ;

Zargarian, D .

CANADIAN JOURNAL OF CHEMISTRY, 2003, 81 (11) :1299-1306

← 1 2 3 4 5 →