SYNTHESIS AND STEREOCHEMICAL BEHAVIOR OF 8-ALKYL-3-(1-PHENYLETHYL)-7-OXA-1,3-DIAZABICYCLO-[3.2.1]-OCTANE-4,6-DIONES DIRECTED TOWARDS THE SYNTHESIS OF ALPHA-SUBSTITUTED BETA-AMINO ACIDS

被引：9

作者：

BRASCHI, I ^{[1
]}

CARDILLO, G ^{[1
]}

TOMASINI, C ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1994年 / 50卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)87007-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereoselective synthesis of enantiomerically pure a-hydroxymethyl p-amino acid derivatives is described starting from a,P-unsaturated acids. The unsaturated adds are transformed through simple steps into chiral perhydropyrimidin-4-ones that are diastereoselectively transformed into [3.2.1]-1,3-diaza-7-oxabicyclooctan-4,6-diones by reaction with LiHMDS. The bicycle 9b is opened by reaction with methanol under acid catalysis and the product 10 is selectively reduced to afford the desired compound.

引用

页码：2955 / 2964

页数：10

共 36 条

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