Asymmetric Synthesis of cis??4??and trans??3??Hydroxypipecolic Acids

C Alegret, X Ginesta, A Riera

Index: Alegret, Carlos; Ginesta, Xavier; Riera, Antoni European Journal of Organic Chemistry, 2008 , # 10 p. 1789 - 1796

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Citation Number: 3

Abstract

Abstract Enantioselective syntheses of cis-4-and trans-3-hydroxypipecolic acids from 2, 3- epoxy-5-hexen-1-ol (7) are described. Regioselective C-3 or C-2 ring opening of the epoxide by the appropriate nitrogen nucleophile is the key step in each route. As enantiomerically enriched epoxy alcohols are readily available in any configuration by Sharpless epoxidation, both enantiomers are equally accessible. This approach was also ...