Lipase-catalyzed preparation of both enantiomers of methyl jasmonate

Hiromasa Kiyota, Emi Higashi, Takanori Koike, Takayuki Oritani

Research output: Contribution to journalArticle

35 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 - May 8 2001
Externally publishedYes

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Enantiomers
enantiomers
Lipases
Lipase
acylation
Acylation
preparation
Stereochemistry
stereochemistry
hydrolysis
acetates
Hydrolysis
Acetates
selectivity
Substrates
configurations
methyl jasmonate

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Lipase-catalyzed preparation of both enantiomers of methyl jasmonate. / Kiyota, Hiromasa; Higashi, Emi; Koike, Takanori; Oritani, Takayuki.

In: Tetrahedron Asymmetry, Vol. 12, No. 7, 08.05.2001, p. 1035-1038.

Research output: Contribution to journalArticle

Kiyota, Hiromasa ; Higashi, Emi ; Koike, Takanori ; Oritani, Takayuki. / Lipase-catalyzed preparation of both enantiomers of methyl jasmonate. In: Tetrahedron Asymmetry. 2001 ; Vol. 12, No. 7. pp. 1035-1038.
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