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Stereoselective Synthesis of (2S,4R)-4-Hydroxypipecolic Acid

✍ Scribed by Ernesto G. Occhiato; Dina Scarpi; Antonio Guarna

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
235 KB
Volume
2008
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

A new synthetic route to enantiopure (2__S__,4__R__)‐4‐hydroxypipecolic acid from commercial ethyl (3__S__)‐4‐chloro‐3‐hydroxybutanoate is reported. The synthesis is based on the Pd‐catalyzed methoxycarbonylation of a 4‐alkoxy‐substituted δ‐valerolactam‐derived vinyl triflate followed by the stereocontrolled hydrogenation of the enamine double bond. The final product was obtained after exhaustive hydrolysis in 20 % yield over 10 steps. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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