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
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.
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页码:2955 / 2964
页数:10
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