Zinc-Catalyzed Enantioselective Hydrosilylation of Ketones and Imines under Solvent-Free Conditions

被引：29
作者：
Szewczyk, Marcin [1 ]
Bezlada, Agata [1 ]
Mlynarski, Jacek [1 ,2 ]
机构：
[1] Jagiellonian Univ, Fac Chem, Ingardena 3, PL-30060 Krakow, Poland
[2] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland
来源：
CHEMCATCHEM | 2016年 / 8卷 / 23期
关键词：
asymmetric synthesis; hydrosilylation; reduction; solvent-free conditions; zinc; ASYMMETRIC HYDROSILYLATION; CARBONYL-COMPOUNDS; EFFICIENT HYDROSILYLATION; IRON; REDUCTION; POLYMETHYLHYDROSILOXANE; METAL; ACETATE; PYBOX; COMPLEXES;
D O I：
10.1002/cctc.201601140
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The zinc acetate promoted asymmetric hydrosilylation of various ketones and imines under solvent-free conditions was examined by using an unprecedented low catalyst loading. Exposure of ketones to 0.05 mol% Zn-based chiral diamine complex in the presence of triethoxysilane afforded enantioenriched alcohols in excellent yields (up to 98%) and enantioselectivities (up to 97% ee). This methodology also allowed for the chemoselective 1,2-reduction of alpha,beta-unsaturated ketones and imines.
引用
收藏
页码：3575 / 3579
页数：5
相关论文
共 59 条
[31]   Chiral zinc catalysts for asymmetric synthesis [J].
Lowicki, Daniel ;
Bas, Sebastian ;
Mlynarski, Jacek .
TETRAHEDRON, 2015, 71 (09) :1339-1394
[32]   Asymmetric Hydrosilylation of Ketones Catalyzed by Zinc Acetate with Hindered Pybox Ligands [J].
Lowicki, Daniel ;
Bezlada, Agata ;
Mlynarski, Jacek .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (2-3) :591-595
[33]  
Lumbroso A., 2013, ANGEW CHEM, V125, P1942
[34]   Catalytic Asymmetric Synthesis of Allylic Alcohols and Derivatives and their Applications in Organic Synthesis [J].
Lumbroso, Alexandre ;
Cooke, Michael L. ;
Breit, Bernhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (07) :1890-1932
[35]  
Marciniec B, 2009, ADV SILICON SCI, V1, P1, DOI 10.1007/978-1-4020-8172-9
[36]   Use of diamines containing the α-phenylethyl group as chiral ligands in the asymmetric hydrosilylation of prochiral ketones [J].
Mastranzo, VM ;
Quintero, L ;
de Parrodi, CA ;
Juaristi, E ;
Walsh, PJ .
TETRAHEDRON, 2004, 60 (08) :1781-1789
[37]   Selective reduction of carbonyl compounds by polymethylhydrosiloxane in the presence of metal hydride catalysts [J].
Mimoun, H .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2582-2589
[38]   Enantioselective reduction of ketones by polymethylhydrosiloxane in the presence of chiral zinc catalysts [J].
Mimoun, H ;
de Saint Laumer, JY ;
Giannini, L ;
Scopelliti, R ;
Floriani, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (26) :6158-6166
[39]   CuH-Catalyzed Enantioselective 1,2-Reductions of α,β-Unsaturated Ketones [J].
Moser, Ralph ;
Boskovic, Zarko V. ;
Crowe, Christopher S. ;
Lipshutz, Bruce H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (23) :7852-+
[40]   An iron-catalysed hydrosilylation of ketones [J].
Nishiyama, Hisao ;
Furuta, Akihiro .
CHEMICAL COMMUNICATIONS, 2007, (07) :760-762
123456