The Journal of Organic Chemistry

Synthesis of. alpha.-halocinnamate esters via solvolytic rearrangement of trichloroallyl alcohols

WJ Kruper Jr, AH Emmons

Index: Kruper, William J.; Emmons, Albert H. Journal of Organic Chemistry, 1991 , vol. 56, # 10 p. 3323 - 3329

Full Text: HTML

Citation Number: 24

Abstract

Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-u- chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement. Michael addition of ammonia to these ester derivatives affords cis-and/or tram-aziridine amides. The facile rearrangement allows the synthesis of d, l-phenylalanine derived from ...