A stereospecific nickel-catalyzed cross-coupling of diarylmethyl ethers has been developed.  Alkyl Grignard reagents are competent nucleophiles in the desired reaction.  The scope of the reaction includes both electron-rich and electron-poor arenes.  Achiral nickel catalysts and optically enriched diaryl alcohol derivatives provide products with inversion of configuration with high stereochemical integrity.  This methodology has been used to prepare biologically active diarylethanes that, to the best of our knowledge, have not previously been synthesized as single enantiomers.

Stereospecific cross-couplings of diarylmethyl ethers to form tertiary stereocenters

243rd National Meeting (2012)

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