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Synthesis of Enantioenriched Triarylmethanes by Stereospecific Cross-Coupling Reactions


  • This work was supported by the University of California Cancer Research Coordinating Committee. B.L.H.T. thanks Allergan for a Graduate Fellowship. M.R.H. thanks the University of California for a Chancellor’s Fellowship and the Ford Family Foundation for a Predoctoral Fellowship. We thank Frontier Scientific and Sigma–Aldrich for the donation of chemicals. Dr. John Greaves is acknowledged for mass spectrometry data. Dr. Joseph Ziller is acknowledged for X-ray crystallography data.


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Coupling with inversion: Chiral diarylmethanol derivatives undergo a stereospecific nickel-catalyzed cross-coupling reaction with aryl Grignard reagents (see scheme). The reaction proceeds with inversion of configuration and high enantiospecificity. The method has been applied to the asymmetric synthesis of a triarylmethane-based anti-cancer compound.

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