Phenyl 2-(Trimethylsilyl)ethynyl Sulfone as a New Vinyl Cation Synthon

Article abstract of DOI:10.1021/jo00145a020

Phenyl 2-(trimethylsilyl)ethynyl sulfone (PhSO2CCSiMe3, 1) is provided as a new vinyl cation synthon for an efficient introduction of the vinyl group to a variety of carbanionic nucleophiles (see Table I), including a highly hindered one, 29, an important precursor for the synthesis of Aspidosperma alkaloids.Another attractive feature of this reagent, which can be easily prepared in a large scale, is particularly demonstrated by its utility under rather strong basic conditions such as NaH, t-BuOK, KF, etc.