Rhodium Disulfoxide Catalyzed 1,4-Addition to Cyclic Olefins

J. J. Bürgi; R. Mariz; M. Gatti; E. Drinkel; X. Luan; S. Blumentritt; A. Linden; R. Dorta

doi:10.1055/s-0029-1216714

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Synfacts 2009(6): 0627-0627
DOI: 10.1055/s-0029-1216714

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Rhodium Disulfoxide Catalyzed 1,4-Addition to Cyclic Olefins

Contributor(s): Hisashi Yamamoto, Pingfan Li
J. J. Bürgi, R. Mariz, M. Gatti, E. Drinkel, X. Luan, S. Blumentritt, A. Linden, R. Dorta*
Universität Zürich, Switzerland

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Publication History

Publication Date:
25 May 2009 (online)

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Significance

New disulfoxide ligands are synthesized and successfully applied to the rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic unsaturated ketones or lactones. Very high chemical yields and enantioselectivities are obtained with less than 1 mol% catalyst loading in this reaction. Mechanistic insights of this new ligand and the origin of enantioselectivity are also discussed.