A practical enantioselective synthesis of ( S)-3-hydroxytetradecanoic acid

( S)-3-Hydroxytetradecanoic acid 1 has been synthesized in an overall yield of 27% from ( S)-epichlorohydrin 2 as follows: (1) regio and chemoselective epoxide opening of 2 with a Grignard reagent under the catalysis by Cu(I) followed by consecutive epoxide formation; (2) regioselective epoxide open...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-07, Vol.10 (15), p.2945-2950
Main Authors: Matsuyama, Keisuke, Ikunaka, Masaya
Format: Article
Language:English
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Summary:( S)-3-Hydroxytetradecanoic acid 1 has been synthesized in an overall yield of 27% from ( S)-epichlorohydrin 2 as follows: (1) regio and chemoselective epoxide opening of 2 with a Grignard reagent under the catalysis by Cu(I) followed by consecutive epoxide formation; (2) regioselective epoxide opening of ( S)-1,2-epoxytridecane 4 with cyanide anion under pH controlled conditions followed by consecutive nitrile hydrolysis with alkaline H 2O 2 gave crude 1; (3) its purification via the N, N-dicyclohexylammonium salt 6. The method thus devised is practical and scalable for the industrial production of 1.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00290-6