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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