Tetrahedron p. 1979 - 1990 (1988)
Update date:2022-08-03
Topics:
Gosselin, Pascal
A new synthetic route to γ-Damascone 1 starting with methyl-γ-dithiocyclogeranate 2 is described.Addition of HMPT was found necessary to perform the carbophilic addition of allylmagnesium bromide on dithioester 2.A dienylsulfide, 6,6-dimethyl-2-methylene-(1-methylthio-1,3-butadiene)-1-yl cyclohexane 3 resulted from this addition, and not the expected dithioketal.Following a number of described conditions, hydrolysis of 3 to γ-damascone 1 proved to be unsatisfactory.These initial attempts but showed the necessity for an acidic medium.This finding allowed the development of a new, very mild method of hydrolysis of dienylsulfides to unsaturated ketones.
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Doi:10.1246/bcsj.61.4347
(1988)Doi:10.1002/ardp.19893220108
(1989)Doi:10.1039/DT9910000949
(1991)Doi:10.1055/s-0034-1378805
(2015)Doi:10.1002/chem.201402524
(2015)Doi:10.1055/s-1988-27781
(1988)
