Hindered organoboron groups in organic chemistry. 25. The condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions to give alkenes

Article abstract of DOI:10.1016/S0040-4020(01)87983-7

In the presence of protic acids the condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions results in alkenes. In the presence of strong acids such as HCl or CF₃SO₃H, the products contain > 90% of E-alkenes in all cases tried. When acetic acid is used, the Z-alkenes may result predominantly, particularly in the cases of R(S)CHO and R(t)CHO.