Reaction of β-Ethylthiopropionyl Tetrafluoroborates with Alkynes. Stereospecific One-pot Synthesis of 1-Ethylthiopent-1,4-dien-3-ones

Valentine G. Nenajdenko; Mikhail V. Lebedev; Elizabeth S. Balenkova

doi:10.1055/s-1995-5198

Synlett 1995; 1995(11): 1133-1134
DOI: 10.1055/s-1995-5198

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Reaction of β-Ethylthiopropionyl Tetrafluoroborates with Alkynes. Stereospecific One-pot Synthesis of 1-Ethylthiopent-1,4-dien-3-ones

Valentine G. Nenajdenko, Mikhail V. Lebedev, Elizabeth S. Balenkova^*

^*Department of Chemistry, Moscow State University, 119899 Moscow, Russia

Abstract

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A stereospecific one-pot synthesis of 1-ethylthiodivinylketones is described. Reaction of different alkynes with β-ethylthiopropionyl tetrafluoroborate proceeds through formation of six-membered cyclic sulfonium salts as a conjugated addition of acyl and sulfide moieties to acetylene. Subsequent cleavage of sulfonium salts with bases results in the corresponding 1-ethylthiodivinylketones. The reaction proceeds regio- and stereospecifically as syn-addition of acryloyl and ethylthio groups to the triple bond.

acylsulfonium salt - conjugate addition - acylation - divinyl ketones - one-pot synthesis

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