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Synthesis 2011(16): 2664-2670  
DOI: 10.1055/s-0030-1260120
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Stereoselective Route to cis-(2S,3R)-3-Hydroxypipecolic Acid and Two Enantiomeric cis-2-Hydroxymethyl-3-hydroxypiperidine Derivatives

Shital K. Chattopadhyay*, Shankar P. Roy, Tapan Saha
Department of Chemistry, University of Kalyani, Kalyani-741235, West Bengal, India
Fax: +91(33)25828282; e-Mail: skchatto@yahoo.com;
Further Information

Publication History

Received 13 May 2011
Publication Date:
14 July 2011 (online)

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Abstract

Stereoselective routes to cis-(2S,3R)-3-hydroxypipecolic acid and two enantiomeric cis-2-hydroxymethyl-3-hydroxypiperidine derivatives from a common precursor have been developed, which featured stereocontrolled vinylation of a α-chiral aldehyde and ring-closing metathesis as key steps.

Key words

amino acids - diastereoselectivity - piperidines - chiral pool - metathesis

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