相转移催化双不对称诱导合成α■氨基酸(Ⅱ)

DOUBLE ASYMMETRIC INDUCTION IN THE SYNTHESIS OF α-AMINO ACID UNDER PTC CONDITIONS(Ⅱ)

在固液两相体系,以手性和非手性季铵盐为相转移催化剂,研究了各种α-溴代脂肪酸龙脑酯与邻苯二甲酰亚胺的Gabriel反应,得到4种具有光学活性的α-邻苯二甲酰亚胺基羧酸酯、以肼解、水解后得到4种具有光学活性的α-氨基酸,光学纯度最高为47.4％,并观察到手性识别和双不对称诱导效应。

Gabriel reaction of potassium phthalimide and (-)-bornyl α- bromocarboxylates are studied under solid-liquid chiral and nonchiral PTC conditions. Four optically active 2-phthalimidoesters are synthesized under varied PTC condi- tions. These N-substituted phthalimide through hydrazinolysis and hydrolysis to give four optically active α-amino acids with optical purity range from 1.7%~47.4%. The evident effect of double asymmetric induction is observed.