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Synfacts 2006(6): 0580-0580  
DOI: 10.1055/s-2006-934476
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Chiral Enones via Asymmetric Allylic Oxidation

Contributor(s): Mark Lautens, Andrew Martins
B. M. Trost*, J. Richardson, K. Yong
Stanford University, USA
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

A variety of π-allyl precursors were enantioselectively oxidized to the corresponding enone using a [(η3-allyl)PdCl]2/Trost ligand catalyst system and a nitronate as the oxidizing agent. Enantioselectivities were excellent for both cyclic meso-allylic carbonates and racemic mixtures of chiral allylic 3,5-dinitrobenzoates. In addition, the reaction is chemoselective to allylic leaving groups, and was used for the kinetic resolution of a racemic allylic carbonate.