Journal of the American Chemical Society 2011-11-16

Chiral allene-containing phosphines in asymmetric catalysis.

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

Index: J. Am. Chem. Soc. 45th ed., 133 , 18066-18069, (2011)

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Abstract

We demonstrate that allenes, chiral 1,2-dienes, appended with basic functionality can serve as ligands for transition metals. We describe an allene-containing bisphosphine that, when 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.