PREPARATION OF (E)-α,β-UNSATURATED AROMATIC ALDEHYDES BY HIGH STEREOSELECTIVE OLEFINFORMYLATION.

Article abstract of DOI:10.1016/S0040-4039(00)94552-0

Treatment of acetaldehyde N-ter-butylimine by two equivalents of LDA, followed by trimethylsilyl chloride trapping affords the α,α-disilylated imine; the latter reacts with aromatic aldehydes producing α,β-ethylenic aldehydes in excellent yields and with very high stereoselectivity in favour of the E isomer.