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Palladium-Catalyzed Annulation Reactions for Diastereoselective Cyclopentene Synthesis

Benjamin L. Kohn and Elizabeth R. Jarvo*

*Department of Chemistry, Univerisity of California-Irvine, 1102 Natural Sciences II, Irvine, California 92697-2025, United States, Email: erjarvouci.edu

B. L. Kohn, E. R. Jarvo, Org. Lett., 2011, 13, 4858-4861.

DOI: 10.1021/ol2019423 (free Supporting Information)



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Abstract

Palladium-catalyzed annulation reactions of conjugate acceptors and allenyl boronic ester provide substituted cyclopentenes in high yields and diastereoselectivities, including polycyclic lactone and lactam products. Reactions are hypothesized to initiate by conjugate addition of a nucleophilic propargylpalladium complex.


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Key Words

Cyclopentenes


ID: J54-Y2011-2650