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
收藏
页码：1559 / 1565
页数：7
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