A new and easy route to (2E,4E)-dienals by four-carbon homologation of aldehydes

Article abstract of DOI:10.1016/S0040-4039(00)73973-6

A new synthetic method of (2E,4E)-dienals by four-carbon homologation of aldehydes is described. γ-trimethylsilyl crotonaldimine 2 , easily generated from N-ter-butyl-crotonaldimine 1, LDA and ClSiMe₃, reacts with aldehydes in the presence of catalytic CsF in DMSO at rt → 100°C to afford homologous aldehydes 3 in good yields and with excellent (E,E)-selectivities.