SYNTHESIS OF (-)-PINIDINE VIA ASYMMETRIC, ELECTROPHILIC ENOLATE HYDROXYAMINATION NITRONE REDUCTION

被引：25

作者：

OPPOLZER, W

MERIFIELD, E

机构：

[1] Département de Chimie Organique, Université de Genève, Genève

来源：

HELVETICA CHIMICA ACTA | 1993年 / 76卷 / 02期

关键词：

D O I：

10.1002/hlca.19930760218

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiomerically pure (-)-pinidine (1) has been synthesized in 18.5% overall yield by a nine-step sequence starting from keto-ester 2. The key step 5 --> 6 involves an asymmetric, electrophilic enolate hydroxyamination. Diastereoselective hydrogenation of nitrone 6 ensures the cis-relation between the substituents at C(2) and C(6) in piperidine 7.

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页码：957 / 962

页数：6

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