Transmetalation as a Route to Novel Styryllithium Reagents
作者:Chinwon Rim、David Y. Son
DOI:10.1021/ol035193k
日期:2003.9.1
[structure: see text] Transmetalation of beta-tributyl(styryl)stannanes with n-BuLi gives the functional equivalents of the corresponding styryllithium intermediates. Reaction of the intermediates with chlorotrimethylsilane, iodomethane, or dimethyl sulfate gives the substituted styryl products in moderate to good yields. In all cases, the configuration about the double bond was retained in the products
Allylsilanes have long been recognized as key molecular building blocks in organicsynthesis that are routinely employed as nucleophilic allylating reagents. Although a great deal of catalytic and stoichiometric synthetic strategies are available to prepare such allylsilanes from prefunctionalized substrates, the use of stable and widely available alkenes as their direct precursors remains underdeveloped