SYNTHESIS OF BETA-GAMMA-UNSATURATED ALPHA-AMINO-ACIDS

被引：12

作者：

NUNAMI, KI ^{[1
]}

SUZUKI, M ^{[1
]}

YONEDA, N ^{[1
]}

机构：

[1] TANABE SEIYAKU CO LTD,RES LAB,YODOGAWA KU 16-89 KASHIMA-3-CHOME,OSAKA 532,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 09期

关键词：

D O I：

10.1039/p19790002224

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Saponification of methyl N-formylcycloalkylideneglycinates (3) gave N-formylcycloalk-1-enylglycines (4) through migration of the double bond. The compounds (4) were converted into cycloalk-1-enylglycines (6) by acid hydrolysis. On the results of mechanistic studies it is supposed that the migration is initiated by intramolecular proton abstraction by the carboxylate ion at the γ-position. The method was extended to the synthesis of cycloalk-1-enylglycines containing heteroatoms in the ring [compounds (15)] and isodehydrovaline (17) in high yields.

引用

页码：2224 / 2229

页数：6

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