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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 20期

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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页码：5370 / 5376

页数：7

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