ASYMMETRIC METAL CARBENE INSERTION INTO THE SI-H BOND

被引:49
作者
LANDAIS, Y
PLANCHENAULT, D
机构
[1] Institut de Chimie Organique, Université de Lausanne, 1005 Lausanne, Rue de la Barre
关键词
D O I
10.1016/S0040-4039(00)60729-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha-Silyl-alpha-substituted acetic esters have been prepared in good yields and reasonable diastereoselectivities using an asymmetric metal carbene insertion into the Si-H bond. Optically active 1,2-diols were then prepared after reduction of the ester and conversion of the C-Si bond into a C-OH bond.
引用
收藏
页码:4565 / 4568
页数:4
相关论文
共 26 条
[1]   HIGHLY STEREOSELECTIVE ACCESS TO 2,4-SUBSTITUTED AND 2,4,5-SUBSTITUTED TETRAHYDROFURANS FROM ALPHA-SILYLACETIC ESTERS - A STUDY OF HOMOALLYLIC STEREOCONTROL [J].
ANDREY, O ;
LANDAIS, Y .
TETRAHEDRON LETTERS, 1993, 34 (52) :8435-8438
[2]   A ONE-POT SYNTHESIS OF ALPHA-(ALKOXYSILYL)ACETIC ESTERS [J].
ANDREY, O ;
LANDAIS, Y ;
PLANCHENAULT, D .
TETRAHEDRON LETTERS, 1993, 34 (18) :2927-2930
[3]   A NEW AND GENERAL-SYNTHESIS OF ALPHA-SILYL CARBONYL-COMPOUNDS BY SI-H INSERTION FROM TRANSITION-METAL CATALYZED-REACTIONS OF DIAZO ESTERS AND DIAZO KETONES [J].
BAGHERI, V ;
DOYLE, MP ;
TAUNTON, J ;
CLAXTON, EE .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6158-6160
[4]   ASYMMETRIC CATALYSIS - MECHANISM OF ASYMMETRIC CATALYTIC INTRAMOLECULAR HYDROSILATION [J].
BERGENS, SH ;
NOHEDA, P ;
WHELAN, J ;
BOSNICH, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2128-2135
[5]  
BERGSTEIN W, 1981, SYNTHESIS-STUTTGART, P76
[6]   VINYLBORANE FORMATION IN RHODIUM-CATALYZED HYDROBORATION OF VINYLARENES - MECHANISM VERSUS BORANE STRUCTURE AND RELATIONSHIP TO SILATION [J].
BROWN, JM ;
LLOYDJONES, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :866-878
[7]   DETERMINATION OF ENANTIOMERIC PURITY OF GLYCOLS RCHOHCH2OH [J].
ELIEL, EL ;
KO, KY .
TETRAHEDRON LETTERS, 1983, 24 (34) :3547-3550
[8]   ENANTIOSELECTIVE SYNTHESIS OF ALPHA-TRIALKYLSILYL KETONES AND ALDEHYDES [J].
ENDERS, D ;
LOHRAY, BB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (04) :351-352
[9]   REGIOSELECTIVE, DIASTEREOSELECTIVE, AND ENANTIOSELECTIVE SYNTHESIS OF VIC-DIOLS VIA ALPHA-SILYL KETONES ACCORDING TO THE SAMP/RAMP HYDRAZONE METHOD [J].
ENDERS, D ;
NAKAI, S .
CHEMISCHE BERICHTE, 1991, 124 (01) :219-226
[10]   A ONE-POT CONVERSION OF THE PHENYLDIMETHYLSILYL GROUP INTO A HYDROXYL GROUP [J].
FLEMING, I ;
SANDERSON, PEJ .
TETRAHEDRON LETTERS, 1987, 28 (36) :4229-4232