128114-20-5Relevant academic research and scientific papers
Addition of Zinc Homoenolates to Acetylenic Esters: A Formal Cycloaddition
Crimmins, Michael T.,Nantermet, Philippe G.
, p. 4235 - 4237 (1990)
Addition of zinc homoenolates to acetylenic esters results in conjugate addition followed by intramolecular acylation of the intermediate allenolate to produce 2-carbalkoxycyclopentenones, formally a cycloaddition, in a single operation.
Addition of Zinc Homoenolates to Acetylenic Esters and Amides: A Formal Cycloaddition
Crimmins, Michael T.,Nantermet, Philippe G.,Trotter, B. Wesley,Vallin, Isabelle M.,Watson, Paul S.,et al.
, p. 1038 - 1047 (2007/10/02)
The copper-catalyzed conjugate addition-cycloacylation reaction of zinc homoenolates with acetylenic esters or acetylenic amides is described.The zinc homoenolate is prepared from 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.
