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

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

Keywords:

• Asymmetric synthesis
• bioactivity
• enantioselectivity
• natural products
• organocatalysis

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.