2021•Journal of the American Chemical SocietyOpen access

Overcoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters

Jianyu Xu, Olivia P. Bercher, Mary P. Watson

Abstract

The use of a simple stilbene ligand has enabled a stereospecific Suzuki-Miyaura cross-coupling of tertiary benzylic carboxylates, including those lacking naphthyl substituents. This method installs challenging all-carbon diaryl quaternary stereocenters in good yield and ee and represents an important breakthrough in the "naphthyl requirement" that pervades stereospecific cross-couplings involving enantioenriched electrophiles.

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Key concepts: Stereocenter, Stereospecificity, Chemistry, Electrophile, Yield (engineering), Quaternary carbon, Stereochemistry, Ligand (biochemistry)