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 DielsāAlder reactions utilizing the vinylsilane functionality demonstrated the reactivity and synthetic utility of oxasilacyclopentenes.