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Catalytic Stereoselective Borylative Transannular Reactions
Author(s) -
Sendra Jana,
Manzano Ruben,
Reyes Efraim,
Vicario Jose L.,
Fernández Elena
Publication year - 2020
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.201913438
Subject(s) - moiety , electrophile , stereocenter , ketone , chemistry , stereochemistry , stereoselectivity , diastereomer , ligand (biochemistry) , michael reaction , catalysis , enantioselective synthesis , organic chemistry , biochemistry , receptor
Medium‐sized carbocycles containing an α,β‐unsaturated ketone moiety as Michael acceptor site and a ketone moiety as internal electrophilic site are ideal substrates to conduct Cu(I)‐catalyzed conjugated borylation followed by electrophilic intramolecular trapping that results into a pioneer transannular borylative ring closing reaction. The relative configuration of three adjacent stereocenters is controlled, giving access to a single diastereoisomer for a wide range of substrates tested. Moreover, when a chiral ligand is incorporated, the reaction provides enantioenriched polycyclic products with up to 99 % ee .