Synthesis and olfactory evaluation of optically active β-alkyl substituted γ-lactones and whiskey lactone analogues

Masashi Kawasaki; Daiki Kato; Takuya Okada; Yuko Morita; Yasuo Tanaka; Naoki Toyooka

doi:10.1016/j.tet.2020.130984

Synthesis and olfactory evaluation of optically active β-alkyl substituted γ-lactones and whiskey lactone analogues

Masashi Kawasaki^*, Daiki Kato, Takuya Okada, Yuko Morita, Yasuo Tanaka, Naoki Toyooka

^*Corresponding author for this work

Life Sciences and Bioengineering

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

3 Scopus citations

Abstract

Optically active β-alkyl substituted γ-lactones and whiskey lactone analogues were synthesized, and the odor properties were evaluated. During the preparation of the chiral intermediates, we found good reaction conditions for the highly enantioselective esterification of 3-arylmethyl-2-methyl-1-propanols to kinetically resolve them. The results of the olfactory evaluations of the synthesized lactones revealed that the alkyl groups on the γ-lactone rings played an important role for the odor profiles.

Original language	English
Article number	130984
Journal	Tetrahedron
Volume	76
Issue number	12
DOIs	https://doi.org/10.1016/j.tet.2020.130984
State	Published - 2020/03/20

Keywords

Asymmetric synthesis
Lactone
Lipase
Odor
Whiskey lactone

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2020.130984

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title = "Synthesis and olfactory evaluation of optically active β-alkyl substituted γ-lactones and whiskey lactone analogues",

abstract = "Optically active β-alkyl substituted γ-lactones and whiskey lactone analogues were synthesized, and the odor properties were evaluated. During the preparation of the chiral intermediates, we found good reaction conditions for the highly enantioselective esterification of 3-arylmethyl-2-methyl-1-propanols to kinetically resolve them. The results of the olfactory evaluations of the synthesized lactones revealed that the alkyl groups on the γ-lactone rings played an important role for the odor profiles.",

keywords = "Asymmetric synthesis, Lactone, Lipase, Odor, Whiskey lactone",

author = "Masashi Kawasaki and Daiki Kato and Takuya Okada and Yuko Morita and Yasuo Tanaka and Naoki Toyooka",

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T1 - Synthesis and olfactory evaluation of optically active β-alkyl substituted γ-lactones and whiskey lactone analogues

AU - Kawasaki, Masashi

AU - Kato, Daiki

AU - Okada, Takuya

AU - Morita, Yuko

AU - Tanaka, Yasuo

AU - Toyooka, Naoki

PY - 2020/3/20

Y1 - 2020/3/20

N2 - Optically active β-alkyl substituted γ-lactones and whiskey lactone analogues were synthesized, and the odor properties were evaluated. During the preparation of the chiral intermediates, we found good reaction conditions for the highly enantioselective esterification of 3-arylmethyl-2-methyl-1-propanols to kinetically resolve them. The results of the olfactory evaluations of the synthesized lactones revealed that the alkyl groups on the γ-lactone rings played an important role for the odor profiles.

AB - Optically active β-alkyl substituted γ-lactones and whiskey lactone analogues were synthesized, and the odor properties were evaluated. During the preparation of the chiral intermediates, we found good reaction conditions for the highly enantioselective esterification of 3-arylmethyl-2-methyl-1-propanols to kinetically resolve them. The results of the olfactory evaluations of the synthesized lactones revealed that the alkyl groups on the γ-lactone rings played an important role for the odor profiles.

KW - Asymmetric synthesis

KW - Lactone

KW - Lipase

KW - Odor

KW - Whiskey lactone

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DO - 10.1016/j.tet.2020.130984

M3 - 学術論文

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SN - 0040-4020

VL - 76

JO - Tetrahedron

JF - Tetrahedron

IS - 12

M1 - 130984

ER -

Synthesis and olfactory evaluation of optically active β-alkyl substituted γ-lactones and whiskey lactone analogues

Abstract

Keywords

ASJC Scopus subject areas

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