Elsevier

Tetrahedron Letters

Volume 50, Issue 26, 1 July 2009, Pages 3489-3492
Tetrahedron Letters

A regioselective reductive cleavage of benzylidene acetal: stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid

https://doi.org/10.1016/j.tetlet.2009.03.007Get rights and content

Abstract

A stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid, starting from d-glucose is described. The key step in the overall synthesis is a highly regioselective reductive cleavage of benzylidene acetal 13 leading to hydroxymethyl piperidine derivative 14.

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Acknowledgments

We thank CSIR, New Delhi, for the financial support and DST-FIST, New Delhi for NMR facilities. P.S.K. thanks CSIR, New Delhi, for a research fellowship. We thank Mr. Ram Kumar for single crystal X-ray analysis.

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