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The Journal of Organic Chemistry

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

WJ Kruper Jr, AH Emmons

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

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被引用次数: 24

摘要

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 ...