Tetrahedron p. 3245 - 3250 (1986)
Update date:2022-09-26
Topics:
Naef, Ferdinand
Decorzant, Rene
α-Damascone (1), a rose fragrance chemical, was synthesized by an allylmagnesium chloride addition to ketene 7 as key step.When the same ketene 7 was reduced by two different aluminium hydride reagents, α-cyclocitral was obtained.The presumed intermediates, enolates II and III, were first trapped as silyl enol ethers and then hydrolyzed with D2O to give the expected α-monodeuterated carbonyl compounds.Mixed aluminium hydride reduction of ketenes is recommended as a facile entry into the chemistry of aldehyde enolates.
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Doi:10.1246/cl.1986.1849
(1986)Doi:10.1016/S0040-4039(00)85134-5
(1986)Doi:10.1016/j.polymer.2015.05.032
(2015)Doi:10.1021/jm800854e
(2008)Doi:10.1246/cl.2008.1046
(2008)Doi:10.1016/j.tetlet.2008.07.102
(2008)
