(4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one as a chiral auxiliary for the diastereoselective alkylation of a new iminic glycine derivative:: practical asymmetric synthesis of α-amino acids

被引:27
|
作者
Guillena, G [1 ]
Nájera, C [1 ]
机构
[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain
关键词
D O I
10.1016/S0957-4166(98)00113-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The lithium enolate of enantiomerically pure N-[bis(methylthio)methylene] glycinate 11 derived from (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one reacts with alkyl halides giving the alkylated derivatives 12 with a high degree of control of the diastereoselectivity. These alkylated systems are easily hydrolyzed to the corresponding cx-amino acids, the chiral auxiliary being recovered. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码:1125 / 1129
页数:5
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