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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 45, 2015 - Issue 13
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Original Articles

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

, &
Pages 1559-1565 | Received 05 Feb 2015, Published online: 08 May 2015
 

Abstract

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 α-aminooxylation followed by Horner–Wardsworth–Emmons olefination in high enantiomeric purity (97% ee) and high overall yield (38%).

GRAPHICAL ABSTRACT

ACKNOWLEDGMENT

The authors are thankful to V. V. Ranade, Head, Chemical Engineering and Process Development Division, for his encouragement and support.

SUPPLEMENTAL MATERIAL

Supplemental data for this article can be accessed on the publisher’s website.

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