Lipase-catalyzed preparation of both enantiomers of methyl jasmonate

Hiromasa Kiyota, Emi Higashi, Takanori Koike, Takayuki Oritani

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    41 Citations (Scopus)

    Abstract

    Preparation of both enantiomeric methyl jasmonates 1 was achieved via lipase-catalyzed resolution of (±)-methyl 7-epicucurbate 3. Lipase P (Amano) provided good selectivity both for acylation of (±)-3 (E = 370) and hydrolysis of the corresponding acetate (E = 41). Resolution of (±)-methyl 6,7-diepicucurbate 2 gave poor results. It was found that the (6R,7S)-configuration was suitable for the selective enzymatic reaction and the C-(3) stereochemistry of the substrate did not influence the enzymatic reaction.

    Original languageEnglish
    Pages (from-to)1035-1038
    Number of pages4
    JournalTetrahedron Asymmetry
    Volume12
    Issue number7
    DOIs
    Publication statusPublished - 2001 May 8

    ASJC Scopus subject areas

    • Catalysis
    • Physical and Theoretical Chemistry
    • Organic Chemistry
    • Inorganic Chemistry

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