A Chiral Bis-Sulfoxide Ligand in Late-Transition Metal Catalysis; Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Electron-Deficient Olefins

Ronaldo Mariz, Xinjun Luan, Michele Gatti, Anthony Linden and Reto Dorta*

*Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057, Zurich, Switzerland, Email: dortaoci.uzh.ch

R. Mariz, X. Luan, M. Gatti, A. Linden, R. Dorta, J. Am. Chem. Soc., 2008, 130, 2172-2173.

DOI: 10.1021/ja710665q (free Supporting Information)

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Abstract

The precatalyst [{(P,R_s,R_s)-p-tol-BINASO}RhCl]₂, which can be synthesized from relatively cheap, commercially available starting materials, shows both excellent reactivity and selectivity in the asymmetric 1,4-addition of arylboronic acids to cyclic α,β-unsaturated ketones and esters.

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Key Words

Conjugate Addition

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ID: J48-Y2008-0440