Allenes in Asymmetric Catalysis: Asymmetric Ring Opening of meso-Epoxides Catalyzed by Allene-Containing Phosphine Oxides

Xiaotao Pu, Xiangbing Qi and Joseph M. Ready*

*Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, Email: joseph.readyutsouthwestern.edu

X. Pu, X. Qi, J. M. Ready, J. Am. Chem. Soc., 2009, 131, 10364-10365.

DOI: 10.1021/ja9041127

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Abstract

An optically active, C2-symmetric allene-containing bisphosphine oxide catalyzes the addition of SiCl₄ to meso-epoxides with high enantioselectivity. The epoxide opening likely involves generation of a Lewis acidic, cationic (bisphosphine oxide)SiCl₃ complex.

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Key Words

Chlorohydrins, Organocatalysis

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ID: J48-Y2009-2240