Formation and utility of oxasilacyclopentenes derived from functionalized alkynes.
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 Diels-Alder reactions utilizing the vinylsilane functionality demonstrated the reactivity and synthetic utility of oxasilacyclopentenes.
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Timothy B
TB
Clark
K A
KA
Woerpel
D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D000480:Alkynes; D003517:Cyclopentanes; D007659:Ketones; D017646:Organosilicon Compounds