Exclusive γ-regio functionalization of crotonaldehyde using γ-trimethylsilyl crotonaldimine. Application to the one pot synthesis of conjugated dienals

Article abstract of DOI:10.1016/0040-4020(96)00165-2

Cesium fluoride mediated reaction of γ-trimethylsilyl N-tert-butyl crotonaldimine 9 with a wide range of aldehydes takes place in DMSO at room temperature and affords exclusive γ-regio functionalized products. Heating (rt to 100°C) the δ-silyloxy imines 11 thus obtained leads, after very mild hydrolysis of the tert-butylimine function, to the conjugated dienals 14 in good yields and with excellent (E,E)-selectivities.