Lipase-catalyzed preparation of both enantiomers of methyl jasmonate

Hiromasa Kiyota; Emi Higashi; Takanori Koike; Takayuki Oritani

doi:10.1016/S0957-4166(01)00169-0

Lipase-catalyzed preparation of both enantiomers of methyl jasmonate

Hiromasa Kiyota, Emi Higashi, Takanori Koike, Takayuki Oritani

Research output: Contribution to journal › Article › peer-review

38 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 language	English
Pages (from-to)	1035-1038
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	12
Issue number	7
DOIs	https://doi.org/10.1016/S0957-4166(01)00169-0
Publication status	Published - May 8 2001
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Lipase-catalyzed preparation of both enantiomers of methyl jasmonate",

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.",

author = "Hiromasa Kiyota and Emi Higashi and Takanori Koike and Takayuki Oritani",

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T1 - Lipase-catalyzed preparation of both enantiomers of methyl jasmonate

AU - Kiyota, Hiromasa

AU - Higashi, Emi

AU - Koike, Takanori

AU - Oritani, Takayuki

PY - 2001/5/8

Y1 - 2001/5/8

N2 - 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.

AB - 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.

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SP - 1035

EP - 1038

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 7

ER -

Lipase-catalyzed preparation of both enantiomers of methyl jasmonate

Abstract

ASJC Scopus subject areas

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