LEWIS ACID-PROMOTED 1,4-ADDITION TO CHIRAL IMIDE DERIVATIVES IN THE SYNTHESIS OF BETA-AMINO ACIDS

被引:93
作者
AMOROSO, R [1 ]
CARDILLO, G [1 ]
SABATINO, P [1 ]
TOMASINI, C [1 ]
TRERE, A [1 ]
机构
[1] UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALY
关键词
D O I
10.1021/jo00073a017
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 1,4-addition of O-benzylhydroxylamine to imides 3 in the presence of various Lewis acids is described. The reaction is performed in CH2Cl2 at -78-degrees-C and affords derivatives 4 and 5 in good chemical yields and in different diastereomeric ratios, depending on the Lewis acid employed. TiCl4 and Me2AlCl give opposite diastereoselectivities. Furthermore, enantiomerically pure beta-amino acid 9 is obtained in good yield from compound 4a.
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页码:5615 / 5619
页数:5
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