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Chiral Allene-Containing Phosphines in Asymmetric Catalysis

Feng Cai, Xiaotao Pu, Xiangbing Qi, Vincent Lynch, Akella Radha and Joseph M. Ready*

*Department of Biochemistry, University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75398-9038, United States, Email: Joseph.readyutsouthwestern.edu

F. Cai, X. Pu, X. Qi, V. Lynch, A. Radha, J. M. Ready, J. Am. Chem. Soc., 2011, 133, 18066-18069.

DOI: 10.1021/ja207748r (free Supporting Information)



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Abstract

Chiral allenes appended with basic functionality can serve as ligands for transition metals. An allene-containing bisphosphine coordinated to Rh(I) promotes the asymmetric addition of arylboronic acids to α-keto esters with high enantioselectivity. Solution and solid-state structural analysis reveals that one olefin of the allene can coordinate to transition metals, generating bi- and tridentate ligands.


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Key Words

arylation, α-hydroxy esters


ID: J48-Y2011-3200