ORGANIC SYNTHESIS USING HALOBORATION REACTION XV. A NEW SYNTHESIS OF α,β-UNSATURATED ESTERS BY THE HIGHLY CHEMOSELECTIVE REACTION OF B-I-9-BBN-ETHOXYETHYNE ADDUCT WITH ALDEHYDES

Article abstract of DOI:10.1016/S0040-4039(01)93472-0

A haloboration adduct, formed by the reaction of B-iodo-9-borabicyclo<3.3.1>nonanes with ethoxyethyne reacts with aldehydes chemoselectively under very mild conditions.The subsequent hydrolytic work-up affords trans-α,β-unsaturated esters in good yields.