F. Naef, R. Decorzant
1986
Citations
0
Influential Citations
18
Citations
Journal
Tetrahedron
Abstract
Abstract 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.