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Palladium-Catalyzed Oxidative Wacker Cyclizations in Nonpolar Organic Solvents with Molecular Oxygen: A Stepping Stone to Asymmetric Aerobic Cyclizations

Raissa M. Trend, Yeeman K. Ramtohul, Eric M. Ferreira, Brian M. Stoltz*

*The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd., MC 164-30, Pasadena, CA 91125, USA, Email: stoltzcaltech.edu

R. M. Trend, Y. K. Ramtohul, E. M. Ferreira, B. Stoltz, Angew. Chem. Int. Ed., 2003, 42, 2892-2895.

DOI: 10.1002/anie.200351196 (free Supporting Information)


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Abstract

Several Pd-catalyzed oxidative cyclizations proceed in excellent yield under simple aerobic conditions. Importantly, this system provided entry into enantioselective catalysis with a readily available Pd-sparteine complex.


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proposed mechanism



Key Words

asymmetric catalysis, homogeneous catalysis, oxidation, oxygen, palladium, lactones, tetrahydrofurans, γ-lactams


ID: J06-Y2003-610