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.

引用

页码：1175 / 1178

页数：4

共 52 条

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