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Regio‐ and Stereospecific 1,3‐Allyl Group Transfer Triggered by a Copper‐Catalyzed Borylation/ ortho ‐Cyanation Cascade
Author(s) -
Yang Yang
Publication year - 2016
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.201508294
Subject(s) - borylation , cyanation , stereocenter , chemistry , stereospecificity , electrophile , cascade , medicinal chemistry , group (periodic table) , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , aryl , alkyl , chromatography
A copper‐catalyzed borylation/ ortho ‐cyanation/allyl group transfer cascade was developed. Initiated by an unconventional copper‐catalyzed electrophilic dearomatization, this process features regio‐ and stereospecific 1,3‐transposition of the allyl fragment enabled by an aromatization‐driven Cope rearrangement. This method provides an effective means for the construction of adjacent tertiary and quaternary stereocenters with excellent diastereocontrol.