The stereospecific cross-coupling of benzylic ethers and lactones via nickel-catalyzed ring openings has been developed. Benzylic ethers undergo nickel-catalyzed ring opening and cross coupling with both alkyl and aryl Grignard reagents with excellent stereochemical fidelity to afford highly substituted, long chain primary alcohols. Enantioenriched lactones similarly undergo stereospecific cross-couplings to afford long chain carboxylic acids. Applications of this methodology to natural product derivitization will be discussed.

Stereospecific cross-coupling reactions via nickel-catalyzed ring opening reactions of benzylic ethers and lactones

248th National Meeting (2014)

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