Bulletin of the Academy of Sciences of the USSR Division of Chemical Science p. 1839 - 1849 (1990)
Update date:2022-07-31
Topics:
Cheskis, B. A.
Ivanova, N. M.
Moiseenkov, A. M.
Nefedov, O. M.
The ZnCl2 catalyzed condensation of 1-trimethylsilyloxyvinylcyclopropane with aldehydes and ketones gave β-silyloxyacylcyclopropanes, which were converted by the action of TsOH in boiling benzene into 1-cyclopropyl-2E-alken-1-ones.Reduction of the latter gave saturated and allyl cyclopropylcarbinols, which by means of Me3SiX and catalytic amounts of ZnX2 (X = Cl, Br) were highly selectively converted into the corresponding linear mono- and dienic E-homoallyl halides.The sequence of reactions that was worked out provided an effective synthesis of 3E-dodecenyl acetate, a sex pheromone of the sugar beet moth.
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