Catalytic asymmetric protonation of lithium enolates using amino acid derivatives as chiral proton sources

被引：29
作者：
Mitsuhashi, K
Ito, R
Arai, T
Yanagisawa, A [1 ]
机构：
[1] Chiba Univ, Grad Sch Sci & Technol, Chiba 2638522, Japan
[2] Chiba Univ, Fac Sci, Dept Chem, Chiba 2638522, Japan
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 08期
关键词：
D O I：
10.1021/ol0603007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric protonation of lithium enolates was examined using commercially available amino acid derivatives as chiral proton sources. Among the amino acid derivatives tested, N beta-L-aspartyl-L-phenylalanine methyl ester was found to cause significant asymmetric induction in the protonation of lithium enolates. The enantiomeric excess (up to 88% ee) of the products obtained in the presence of a catalytic amount of the chiral proton source was higher than those obtained in the stoichiometric reaction.
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页码：1721 / 1724
页数：4
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