A New Organosilicon Reagent for One-Pot Conversion of Aldehydes into Trienals

Abstract

The 6-trimethylsilyle N-tert-butyl sorbaldimine was easily prepared from sorbaldimine throught deprotonation with LDA in THF at −60°C and subsequent trapping of the organo lithium intermediate by trimethylsilylchloride. The condensation of this new organosilicon reagent with several aldehydes, in the presence of catalytic CsF in DMSO at 100°C leads directly, after the hydrolysis of the imine function, to the expected trienals in good yields and with excellent E selectivity.