A stereospecific cross-coupling of secondary ethers with alkyl and aryl Grignard reagents has been developed.  Achiral nickel catalysts are used to form tertiary stereocenters from optically enriched secondary alcohol derivatives.  The transformation proceeds with inversion of configuration and high stereochemical integrity, and has been applied to the synthesis of biologically active diaryl- and triarylmethanes.  The scope of the reaction and mechanistic considerations will be discussed.

Stereospecific cross-couplings of alkyl ethers to form tertiary stereocenters

241st National Meeting (2011)

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