MICHAEL-TYPE ADDITION OF PHTHALIMIDE SALTS TO CHIRAL ALPHA,BETA-UNSATURATED IMIDES

被引：37

作者：

CARDILLO, G ^{[1
]}

DESIMONE, A ^{[1
]}

GENTILUCCI, L ^{[1
]}

SABATINO, P ^{[1
]}

TOMASINI, C ^{[1
]}

机构：

[1] UNIV BOLOGNA,CSFM,I-40126 BOLOGNA,ITALY

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(00)73317-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of (R)-(-)-3-aminobutanoic acid starting from chiral alpha,beta-unsaturated imide 1b is described, by means of the nucleophilic attack of several phthalimido derivatives in the presence of a Lewis acid. The reaction was studied in some details and chloromagnesium phthalimide afforded the better results with 95:5 diastereomeric ratio and 90% yield. Furthermore the resulting enolate was trapped performing the reaction in the presence of benzenesulfonyl bromide and the 2-bromo-3-phthalimido derivative 4 was obtained in good yield and high diastereoselectivity and successively transformed into the corresponding 2-azido-3-phthalimido derivative 6 by displacement of the bromide with sodium azide.

引用

页码：5051 / 5054

页数：4

共 12 条

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