Open AccessOvercoming 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.