Chiral tricyclic iminolactone derived from (1R)-(+)-camphor as a glycine equivalent for the asymmetric synthesis of α-amino acids

被引：46
|
作者：
Xu, PF
Chen, YS
Lin, SI
Lu, TJ [1 ]
机构：
[1] Natl Chung Hsing Univ, Dept Chem, Taichung 40227, Taiwan
[2] Lanzhou Univ, Coll Chem & Chem Engn, Natl Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 07期
关键词：
D O I：
10.1021/jo011139a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of a highly efficient and stereoselective methodology for the preparation of alpha-amino acids is described. The chiral template, tricyclic iminolactone 7, was synthesized from (1R)-(+)camphor in five steps in 50% overall yield. Alkylation of iminolactone 7 afforded the CL-monosubstituted products in good yields (74-96%) and excellent diastereoselectivities (>98%). Hydrolysis of the alkylated iminolactones furnished the desired alpha-amino acids in good yields and enantioselectivities with nearly quantitative recovery of the chiral auxiliary 4.
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收藏
页码：2309 / 2314
页数：6
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