Synthesis of conformationally constrained hydroxy-α-amino acids by intramolecular conjugate addition

被引：6
|
作者：
Avenoza, A
Busto, JH
Cativiela, C
Peregrina, JM
机构：
[1] Univ La Rioja, Dept Quim, Logrono, Spain
[2] Univ Zaragoza, CSIC, Inst Ciencia Mat Aragon, Dept Quim Organ, Zaragoza, Spain
来源：
AMINO ACIDS | 2000年 / 18卷 / 02期
关键词：
amino acids; 5(4H)-oxazolone; Diels-Alder reaction; intramolecular conjugate addition; hydroxy-alpha-amino acids;
D O I：
10.1007/s007260050010
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
An efficient and easily applicable method for the synthesis of a variety of hydroxy-alpha-amino acids analogues of serine and phenylalanine has been established. The method involves the stereoselective intramolecular conjugate addition of the benzamide group to cyclohexenone promoted by Lewis acid. Subsequent transformations of functional groups provide the conformationally constrained 2-hydroxy- and 2,4-dihydroxy-6-phenylcyclohexane-alpha-amino acids.
引用
收藏
页码：117 / 127
页数：11
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