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Alkynes as Synthetic Equivalents to Stabilized Wittig Reagents: Intra- and Intermolecular Carbonyl Olefinations Catalyzed by Ag(I), BF3, and HBF4

Jong Uk Rhee and Michael J. Krische*

*Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, Email: mkrischemail.utexas.edu

J. U. Rhee, M. J. Krische, Org. Lett., 2005, 7, 2493-2495.

DOI: 10.1021/ol050838x (free Supporting Information)


Abstract

The use of cationic silver (AgSbF4) as a catalyst for intra- and intermolecular alkyne-carbonyl coupling is described. Intermolecular coupling proceeds stereoselectively to afford trisubstituted enones.

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Key Words

Olefination, Enones, 3-Pyrrolines, 2,5-Dihydrofurans, Cyclopentenes


ID: J54-Y2005-640