相转移催化反应合成脂肪族α-氨基酸

SYNTHESIS OF ALIPHATICα-AMINO ACIDS FROM CHLOROFORM,ALIPHATIC ALDEHYDES(OR KETONES)AND AQUEOUS AMMONIA UNDER TWO-PHASE CONDITIONS

本文利用相转移催化反应由脂肪族醛或酮、氯仿和氨合成了九个脂肪族α-氨基酸,产率21.4—52.4%。直链脂肪醛也能起反应。付产物α-氨基酰胺的离析,为环氧化物中间体历程提供了新的证据。

The reaction of chloroform, aliphatic aldehydes (or ketones) and aqueous ammonia in the presence of triethylbenzyl ammonium chloride and lithium chloride under two-phase conditions was studied.Optimum reaction conditions were determined with cyclohexanone. Under these conditions straightchain aliphatic aldehydes also undergo the reaction. Nine aliphatic α-amino acids were prepared and the yields range from 21.4% to 52.4%.The isolation of by-product a-amino amide (2-amino-2-methyl-n-valer-amide) demonstrates that the reaction involves the formation of an intermediate epoxide followed by the opening of the epoxide ring by ammonia.