Recent Advances in the Transition-Metal-Catalyzed Enantioselective Synthesis of Silicon-Stereogenic Organosilanes

被引:91
作者
Shintani, Ryo [1 ]
机构
[1] Univ Tokyo, Grad Sch Engn, Dept Chem & Biotechnol, Bunkyo Ku, Tokyo 1138656, Japan
关键词
asymmetric catalysis; desymmetrization; hydrosilylation; organosilanes; silicon stereocenters; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; RHODIUM COMPLEXES; SILANES; HYDROSILYLATION; DESYMMETRIZATION; DERIVATIVES; SILACYCLOBUTANES; DIBENZOSILOLES; ALCOHOLYSIS;
D O I
10.1002/ajoc.201500066
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric catalysis is one of the most attractive and efficient ways of synthesizing chiral enantioenriched compounds from achiral precursors. Compared with the well-investigated enantioselective preparation of carbon-stereogenic compounds, the corresponding preparation of silicon-stereogenic compounds is much less established. In particular, the available methods typically rely on the use of stoichiometric amounts of chiral reagents, and little progress has been made on catalytic enantioselective synthesis using prochiral organosilanes until recently. This Focus Review highlights recent advances in the catalytic enantioselective preparation of silicon-stereogenic organosilanes under transition-metal catalysis through desymmetrization of prochiral organosilanes including diorganodihydrosilanes and tetraorganosilanes.
引用
收藏
页码:510 / 514
页数:15
相关论文
共 35 条
[1]   ASYMMETRIC HYDROSILYLATION OF KETONES CATALYZED BY A CHIRAL RHODIUM COMPLEX [J].
CORRIU, RJP ;
MOREAU, JJE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 64 (03) :C51-C54
[2]  
CORRIU RJP, 1973, TETRAHEDRON LETT, P4469
[3]   ASYMMETRIC SYNTHESIS AT SILICON .3. ALCOHOLYSIS OF PROCHIRAL ORGANOSILICON COMPOUNDS CATALYZED BY RHODIUM COMPLEXES [J].
CORRIU, RJP ;
MOREAU, JJE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 120 (03) :337-346
[4]  
HAYASHI T, 1974, TETRAHEDRON LETT, P331
[5]  
Igawa K., 2010, ANGEW CHEM, V122, P740
[6]  
Igawa K., 2012, Angew. Chem, V124, P12917
[7]   Catalytic Enantioselective Synthesis of Alkenylhydrosilanes [J].
Igawa, Kazunobu ;
Yoshihiro, Daisuke ;
Ichikawa, Nobumasa ;
Kokan, Naoto ;
Tomooka, Katsuhiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (51) :12745-12748
[8]   Asymmetric Synthesis of Chiral Silacarboxylic Acids and Their Ester Derivatives [J].
Igawa, Kazunobu ;
Kokan, Naoto ;
Tomooka, Katsuhiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (04) :728-731
[9]   Enantioselective Synthesis of Silanol [J].
Igawa, Kazunobu ;
Takada, Junko ;
Shimono, Tomohiro ;
Tomooka, Katsuhiko .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (48) :16132-+
[10]  
Kuninobu Y., 2013, Angew. Chem., V125, P1560