Journal of Organic Chemistry p. 1038 - 1047 (1993)
Update date:2022-08-03
Topics:
Crimmins, Michael T.
Nantermet, Philippe G.
Trotter, B. Wesley
Vallin, Isabelle M.
Watson, Paul S.
et al.
The copper-catalyzed conjugate addition-cycloacylation reaction of zinc homoenolates with acetylenic esters or acetylenic amides is described.The zinc homoenolate is prepared from <(ethoxycyclopropyl)oxy>trimethylsilane and zinc chloride in ether.Addition of an acetylenic amide or ester provides 2-carboxamido- or 2-carboalkoxy-3-alkylcyclopent-2-en-1-ones in good to excellent yields.The reaction can be carried out in the presence of a variety of sensitive functional groups including epoxides, α,β-unsaturated esters, acetals, silyl ethers, and furans.
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