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Synthesis of Axially Chiral Biaryls through Sulfoxide‐Directed Asymmetric Mild CH Activation and Dynamic Kinetic Resolution
Author(s) -
Hazra Chinmoy Kumar,
Dherbassy Quentin,
WencelDelord Joanna,
Colobert Françoise
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201407865
Subject(s) - enantiopure drug , kinetic resolution , diastereomer , sulfoxide , chemistry , combinatorial chemistry , stereoselectivity , resolution (logic) , axial symmetry , transformation (genetics) , stereochemistry , catalysis , organic chemistry , enantioselective synthesis , computer science , mathematics , biochemistry , geometry , artificial intelligence , gene
A mild and robust direct CH functionalization strategy has been applied to the synthesis of axially chiral biaryls. Such an efficient and stereoselective transformation occurs through an original dynamic kinetic resolution pathway enabling the conversion of diastereomeric mixtures of non‐prefunctionalized substrates into atropisomerically pure, highly substituted biaryl scaffolds. The main feature of this transformation is the use of an enantiopure sulfoxide as both chiral auxiliary and traceless directing group. The potential of newly synthesized biaryls as valuable building blocks is further illustrated.