Base-Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp3)C(sp2) Bond-Forming Reaction

摘要

Alkylaryl- and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 °C, 1 h) to give regio- and stereoselectively the (E)-β--ethylenic ketones ((E)-3-buten-1-ones) in 61–84 % yields and with approximately 100 % stereoselectivity. This vinylation represents a new C(sp3)C(sp2) bond-forming reaction of high synthetic potential.