DIASTEREOFACIAL SELECTIVITY IN REDUCTION OF CHIRAL TETRAMIC ACIDS

被引:52
作者
GALEOTTI, N [1 ]
PONCET, J [1 ]
CHICHE, L [1 ]
JOUIN, P [1 ]
机构
[1] CTR CNRS,UPR 9023,MECAN MOLEC COMMUN CELLULAIRES LAB,INSERM,RUE CARDONVILLE,F-34094 MONTPELLIER 05,FRANCE
关键词
D O I
10.1021/jo00072a018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reduction of (5S)-5-alkyl-2,4-dioxopyrrolidines, so-called tetramic acids, by NaBH4 gives only partial diastereofacial selectivity in the case of the N-substituted analogues 9f-i, unlike the carbamate derivatives 9a-3 which give the reduced cis-pyrrolidinones 10betaa-e. Increasing the steric hindrance of either the N- or C-5-substituents enhances the re-face selectivity. On the other hand, reduction of the heterobicyclic compound 9n leads to a dramatic reversal of the stereoselectivity. Preliminary calculations show that the N-atom of the ring is slightly pyramidalized; the direction of hydride addition could be a consequence of this finding.
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收藏
页码:5370 / 5376
页数:7
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