Resolution of Homoallylic Alcohols Containing Dithioketene Acetal Functionalities. Synthesis of Optically Active .gamma.-Lactones by a Combination of Chemical and Enzymic Methods | Zendy

Yuan-Chi Pai | Zendy; JimMin Fang | Zendy; ShihHsiung Wu | Zendy

Open Access

Resolution of Homoallylic Alcohols Containing Dithioketene Acetal Functionalities. Synthesis of Optically Active .gamma.-Lactones by a Combination of Chemical and Enzymic Methods

Author(s) -

Yuan-Chi Pai,

JimMin Fang,

ShihHsiung Wu

Publication year - 1994

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo00099a036

Subject(s) - chemistry , acetal , optically active , organic chemistry , resolution (logic) , chemical synthesis , combinatorial chemistry , biochemistry , programming language , computer science , in vitro

Racemic homoallylic alcohols 1-3 containing dithioketeneacetal functionalities were prepared by addition of aldehydes to the allylic anions of ketene dithioacetals or 2-alkenyl-1,3-dithiane in a regioand stereoselective manner. Lipase-catalyzed hydrolyses of the corresponding acetates 7-9 afforded optically active alcohols 1-3, which were treated with mercuric chloride to give y-lactones such as natural hop lactone, whiskey lactone, and cognac lactone.

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