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

Jianyu Xu | Zendy; Olivia P. Bercher | Zendy; Mary P. Watson | Zendy

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

Author(s) -

Jianyu Xu,

Olivia P. Bercher,

Mary P. Watson

Publication year - 2021

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.1c03898

Subject(s) - stereocenter , stereospecificity , chemistry , electrophile , yield (engineering) , quaternary carbon , stereochemistry , ligand (biochemistry) , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , biochemistry , materials science , receptor , metallurgy

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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