10.1021/ja047498f.s001 Timothy B. Clark Timothy B. Clark K. A. Woerpel K. A. Woerpel Formation and Utility of Oxasilacyclopentenes Derived from Functionalized Alkynes American Chemical Society 2004 vinylsilane functionality diastereoselective hydrogenation utility Functionalized Alkynes Oxasilacyclopentenes regioselective formation Oxasilacyclopentenes Derived oxasilacyclopentene carbonyl compounds alkyne allylic alcohols 2004-08-11 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Formation_and_Utility_of_Oxasilacyclopentenes_Derived_from_Functionalized_Alkynes/3328951 Oxasilacyclopentenes were shown to be synthetically useful masked allylic alcohols constructed in high yields and regioselectivities from terminal and internal alkynes. Several functional groups were shown to be tolerated utilizing silver-catalyzed silacyclopropenation of alkynes. In situ insertion of various carbonyl compounds into silacyclopropenes afforded regioselective formation of oxasilacyclopentenes. Elaboration of the oxasilacyclopentenes displayed the synthetic utility of these substrates. Both diastereoselective hydrogenation and Dielsāˆ’Alder reactions utilizing the vinylsilane functionality demonstrated the reactivity and synthetic utility of oxasilacyclopentenes.