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

被引：94

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 21期

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.

引用

页码：5615 / 5619

页数：5

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