Development of reactions of silacyclopropanes as new methods for stereoselective organic synthesis

被引:106
作者
Franz, AK [1 ]
Woerpel, KA [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
D O I
10.1021/ar9900562
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this Account, we describe the development of stereospecific, stereoselective, regioselective, and chemoselective carbon-carbon bond-forming reactions of silacyclopropanes that occur under mild conditions. By appropriate choice of metal salt catalyst, the regiochemistry of these reactions may be tuned to give the desired product. Stereoselective nucleophilic substitution reactions and stereospecific oxidation of the C-Si bond to a carbon-oxygen bond demonstrate that the products of these reactions serve as useful intermediates for the synthesis of polyoxygenated organic molecules.
引用
收藏
页码:813 / 820
页数:8
相关论文
共 67 条
[1]  
[Anonymous], CATALYTIC ASYMMETRIC
[2]   ORGANO-METALLIC REACTION-MECHANISMS .18. CONCERNING THE NATURE OF THE TRANSITION-STATE IN THE REACTION OF TRIALKYLALUMINUM COMPOUNDS WITH KETONES [J].
ASHBY, EC ;
SMITH, RS .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 225 (01) :71-85
[3]  
BEAR TJ, UNPUB
[4]   REACTIONS OF A CYCLOTRISILANE WITH OLEFINS AND DIENES - EVIDENCE FOR AN EQUILIBRIUM BETWEEN SILYLENES AND A CYCLOTRISILANE [J].
BELZNER, J ;
IHMELS, H ;
KNEISEL, BO ;
GOULD, RO ;
HERBSTIRMER, R .
ORGANOMETALLICS, 1995, 14 (01) :305-311
[5]  
BLAIR SA, UNPUB
[6]   1/2-ADDUCTS FROM SILYLENES AND 1,3-BUTADIENE [J].
BOBBITT, KL ;
GASPAR, PP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 499 (1-2) :17-26
[7]   STEREOCHEMISTRY AND REGIOCHEMISTRY OF ALDEHYDE INSERTIONS INTO THE C-SI BONDS OF SILIRANES [J].
BODNAR, PM ;
PALMER, WS ;
SHAW, JT ;
SMITROVICH, JH ;
SONNENBERG, JD ;
PRESLEY, AL ;
WOERPEL, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (42) :10575-10576
[8]   Stereo- and regioselectivity of reactions of siliranes with aldehydes and related substrates [J].
Bodnar, PM ;
Palmer, WS ;
Ridgway, BH ;
Shaw, JT ;
Smitrovich, JH ;
Woerpel, KA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4737-4745
[9]   SYNTHESES, STRUCTURES, AND REACTIONS OF SULFUR AND SELENIUM INSERTION PRODUCTS OF 1,1-DI-TERT-BUTYLSILIRANES [J].
BOUDJOUK, P ;
BLACK, E ;
KUMARATHASAN, R ;
SAMARAWEERA, U ;
CASTELLINO, S ;
OLIVER, JP ;
KAMPF, JW .
ORGANOMETALLICS, 1994, 13 (09) :3715-3727
[10]   CONVENIENT ROUTES TO DI-TERT-BUTYLSILANEDIYL - CHEMICAL, THERMAL AND PHOTOCHEMICAL GENERATION [J].
BOUDJOUK, P ;
SAMARAWEERA, U ;
SOORIYAKUMARAN, R ;
CHRUSCIEL, J ;
ANDERSON, KR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1988, 27 (10) :1355-1356