4.7 Article

Organocatalytic Dimerization of Ketoketenes

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JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 4, 页码 1777-1780

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AMER CHEMICAL SOC
DOI: 10.1021/jo8024785

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  1. Oakland University

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A general method for the catalytic dimerization of ketoketenes is described. Tri-n-butylphosphine was found to be the optimal organocatalyst for the racemic reaction. When lithium iodide was used as an additive, the reaction was rendered selective for dimer formation (dimer/trimer >= 16:1). Ring-opening reactions of the ketoketene dimers as well as preliminary studies toward the development of an asymmetric variant are also reported.

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