We describe development of stereospecific nickel-catalyzed coupling reactions.  Benzylic ethers serve as electrophiles and undergo nickel-catalyzed Kumada, Suzuki, Negishi, and multi-step catalytic reactions.  Reactions are highly enantiospecific, and typically proceed with inversion at the benzylic stereogenic centers.  The results of mechanistic experiments are consistent with rate-determining oxidative addition.  Discovery of compounds that exhibit selective anti-cancer activity will also be reported.

Nickel-catalyzed enantiospecific reactions of benzylic ethers

248th National Meeting (2014)

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