Synthesis 2000; 2000(14): 2106-2112
DOI: 10.1055/s-2000-8710
special topic
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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: [email protected]
Further Information

Publication History

Publication Date:
31 December 2000 (online)

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.