STEREOSELECTIVE SYNTHESIS OF VINYLSILANES FROM ALKYNYLSILANES VIA HYDROMAGNESIATION. APPLICATION TO A SYNTHESIS OF 7(E)-DODECENYL ACETATE AND DIHYDROJASMONE

Article abstract of DOI:10.1016/S0040-4039(00)81598-1

Hydromagnesiation of 1-trimethylsilyl-1-alkynes with isobutylmagnesium bromide in the presence of a catalytic amount of Cp2TiCl2 followed by treatment of the resulting vinyl Grignard reagents with alkyl iodides and copper iodide affords (Z)-1,2-dialkyl-vinylsilanes in excellent yields.The utility of the reaction sequence is illustrated by a simple synthesis of 7(E)-dodecenyl acetate and dihydrojasmone.