Asymmetric synthesis of 2,4,5-trisubstituted piperidines from sulfinimine-derived δ-amino β-ketoesters.: Formal synthesis of pseudodistomin B triacetate

被引：46

作者：

Davis, FA ^{[1
]}

Zhang, JY ^{[1
]}

Li, YX ^{[1
]}

Xu, H ^{[1
]}

DeBrosse, C ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 14期

关键词：

D O I：

10.1021/jo050373o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Sulfinyl delta-amino beta-ketoester enaminones, a new sulfinimine-derived chiral building block, undergoes, on hydrolysis in one pot, an intramolecular Michael addition followed by a retro-Michael-type elimination to give enantiopure 2,4,5-trisubstituted piperidines, a structural motif found in numerous biologically active alkaloids. This new chiral building block is readily prepared by treating N-sulfinyl delta-amino beta-ketoesters with dimethylformamide dimethyl acetal. This new protocol was illustrated with a concise formal asymmetric synthesis of marine alkaloid pseudodistomin B triacetate.

引用

页码：5413 / 5419

页数：7

共 33 条

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