Lipase-catalyzed preparation of both enantiomers of methyl jasmonate

Hiromasa Kiyota, Emi Higashi, Takanori Koike, Takayuki Oritani

Research output: Contribution to journalArticle

37 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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