THE DIMESITYLBORON GROUP IN ORGANIC SYNTHESIS. 3. REACTIONS OF ALLYLDIMESITYLBORANE

Article abstract of DOI:10.1016/S0040-4039(00)81483-5

Allyldimesitylborane readily yields an anion that is attacked by electrophiles in a regio- and stereospecific fashion.Alkylation is at the γ-position to give trans-vinylboranes that can be oxidised to aldehydes.Reaction with trimethylsilyl chloride gives the new, highly differentiated three carbon synthon, Mes2BCH^t:CHCH2SiMe3 also by γ-attack and reaction with benzaldehyde proceeds similarly to give rise to a novel γ-lactol synthesis.