Highly Stereoselective Preparation of β-(Organotelluro)acroleins and Facile Stereospecific Synthesis of Conjugated Dienols

Article abstract of DOI:10.1016/0040-4039(95)00580-6

Diorganoditellurides 1 (1a R=n-Bu; 1b R=Ph), by treated with sodium borohydride, reacted with propargylaldehyde to give corresponding β-(organotelluro)acroleins 2 with high (Z)-stereoselectivity in good yields (2a: Z:E=89:11; 2b: pure Z-isomer); Tellurides 3, on treatment with n-BuLi, reacted with carbonyl compounds to afford conjugated dienols with retention of olefin geometry in high yields.