STEREOCONTROLLED CYCLOPROPANATION OF ALPHA,BETA-UNSATURATED CARBOXAMIDES DERIVED FROM BICYCLIC AMINO-ALCOHOLS

被引：17
|
作者：
TANAKA, K
UNO, H
OSUGA, H
SUZUKI, H
机构：
[1] Department of Chemistry, Faculty of Science, Kyoto University, Sakyo, Kyoto
来源：
TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 07期
关键词：
D O I：
10.1016/0957-4166(94)80150-9
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The asymmetric cyclopropanation of the exo-N-[(1R,2S,3R,4S)-2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]hept-3-yl]-3-phenyl-2-propenamide and the endo-( 1R,2R,3S,4S)-isomer with Et(2)Zn/CH2I2 proceeded with predictable absolute stereochemistry. The exo-amide gave the (1R,2R)-cyclopropane derivative selectively (de less than or equal to 80%), while the endo-amide gave the (1S,2S)-isomer (de less than or equal to 58%). Complete reversal of the stereoselectivity (98% de) was observed when O-triisopropyl derivatives of the amides were used in the cyclopropanation.
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页码：1175 / 1178
页数：4
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