A Simple and Highly Stereoselective Route to E-α,β-Unsaturated Aldehydes

Article abstract of DOI:10.1021/jo00061a027

Zinc bromide mediated reaction of α,α-bis(trimethylsilyl)-tert-butylacetaldimine (3) with a wide range of aldehydes takes place under mild conditions and affords the corresponding α,β-unsaturated aldehydes in good yields and with high E stereoselectivity (>98percent).This procedure is successfully applied to the preparation of intermediates for retinoid and natural product synthesis.