Direct organocatalytic asymmetric aldol reactions of α-amino aldehydes:: Expedient syntheses of highly enantiomerically enriched anti-β-hydroxy-α-amino acids

被引：141
|
作者：
Thayumanavan, R
Tanaka, F
Barbas, CF
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
[3] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
来源：
ORGANIC LETTERS | 2004年 / 6卷 / 20期
关键词：
D O I：
10.1021/ol0485417
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient method for the synthesis of highly enantiomerically enriched beta-hydroxy-alpha-amino acid derivatives has been developed. Direct asymmetric aldol reactions of a glycine aldehyde (aminoacetaldehyde) derivative have been performed under organocatalysis using L-proline or (5)-5-pyrrolidine-2-yl-1H-tetrazole. The reactions afforded anti-beta-hydroxy-alpha-amino aldehydes in good yield with high diastereoselectivity (dr up to >100:1) and high enantioselectivity (up to >99.5% ee), which were easily transformed into beta-hydroxy-alpha-amino acid derivatives.
引用
收藏
页码：3541 / 3544
页数：4
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