Asymmetric Synthesis of the Four Stereoisomers of 4-Hydroxypipecolic Acid

Franklin A. Davis; Tianan Fang; Bin Chao; David M. Burns

doi:10.1055/s-2000-8710

Synthesis 2000; 2000(14): 2106-2112
DOI: 10.1055/s-2000-8710

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Asymmetric Synthesis of the Four Stereoisomers of 4-Hydroxypipecolic Acid

Franklin A. Davis^* , Tianan Fang, Bin Chao, David M. Burns

^*Department of Chemistry, Temple University, Philadelphia, PA 19122, USA; Fax +1(215)2 04 15 32; E-mail: fdavis@astro.ocis.temple.edu

Abstract

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The asymmetric synthesis of all four stereoisomers of 4-hydroxypipecolic acid (1) from the polyfunctionalized chiral building blocks δ-amino β-keto esters (S _S, R)-(+)-5 or (R _s, S)-(-)-5 is described. Key steps in the synthesis are the stereoselective reductions of b-phenylpiperidine-2,4-dione (6) and N-sulfinyl δ-amino β-keto esters 5 to cis-4-hydroxy 2-piperidinone 7 and syn-δ-amino β-hydroxy ester 9, respectively. The only protecting/deprotecting group chemistry required is related to the oxidation step.

stereoselective reductions - hydrides - cyclization - asymmetric synthesis - piperidines

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