Concise Enantioselective Synthesis of Naturally Active (S)-3-Hydroxypiperidine

被引：6

作者：

Dey, Soumen ^{[1
]}

Karabal, Pratibha U. ^{[1
]}

Sudalai, Arumugam ^{[1
]}

机构：

[1] CSIR Natl Chem Lab, Chem Engn & Proc Dev Div, Pune 411008, Maharashtra, India

来源：

SYNTHETIC COMMUNICATIONS | 2015年 / 45卷 / 13期

关键词：

Asymmetric synthesis; bioactivity; enantioselectivity; natural products; organocatalysis; ASYMMETRIC ALPHA-AMINOOXYLATION; KINETIC RESOLUTION; TERMINAL EPOXIDES; AMINOXYLATION; ALCOHOLS; OLEFINATION; AMINATION; ALDEHYDES; 1,2-DIOLS; FACILE;

D O I：

10.1080/00397911.2015.1033428

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short and efficient enantioselective synthesis of natural product (S)-3-hydroxypiperidine has been achieved starting from commercially available raw materials employing two catalytic routes: (i) cocatalyzed hydrolytic kinetic resolution (HKR) of racemic methyl-3-(oxiran-2-yl)propanoate; (ii) proline-catalyzed -aminooxylation followed by Horner-Wardsworth-Emmons olefination in high enantiomeric purity (97% ee) and high overall yield (38%).

引用

页码：1559 / 1565

页数：7

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