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

被引：1

作者：

Kawasaki, Masashi ^{[1
]}

Kato, Daiki ^{[2
]}

Okada, Takuya ^{[2
]}

Morita, Yuko ^{[3
]}

Tanaka, Yasuo ^{[4
]}

Toyooka, Naoki ^{[2
]}

机构：

[1] Toyama Prefectural Univ, Fac Engn, Ctr Liberal Arts & Sci, 5180 Kurokawa, Imizu, Toyama 9390398, Japan

[2] Univ Toyama, Grad Sch Sci & Engn, 3190 Gofuku, Toyama 9308555, Japan

[3] Toyama Prefectural Univ, Coll Technol, Dept Bioresources Sci, 5180 Kurokawa, Imizu, Toyama 9390398, Japan

[4] TAIYO CORP, Yodogawa Ku, 1-6-27 Higashiawaji, Osaka 5330023, Japan

来源：

TETRAHEDRON | 2020年 / 76卷 / 12期

关键词：

Asymmetric synthesis; Lactone; Lipase; Odor; Whiskey lactone; CATALYTIC ASYMMETRIC-SYNTHESIS; LIPASE-MEDIATED PREPARATION; PSEUDOMONAS-CEPACIA; SENSORY PROPERTIES; ODOR PROPERTIES; ENANTIOSELECTIVE SYNTHESES; VOLATILE COMPONENTS; ENANTIOMERS; ISOMERS; HYDROGENATION;

D O I：

10.1016/j.tet.2020.130984

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active beta-alkyl substituted gamma-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 gamma-lactone rings played an important role for the odor profiles. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：10

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