Premium
Lewis Acid Catalyzed Borotropic Shifts in the Design of Diastereo‐ and Enantioselective γ‐Additions of Allylboron Moieties to Aldimines
Author(s) -
van der Mei Farid W.,
Miyamoto Hiroshi,
Silverio Daniel L.,
Hoveyda Amir H.
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.201600546
Subject(s) - aldimine , enantioselective synthesis , catalysis , lewis acids and bases , chemistry , organic chemistry , combinatorial chemistry
Catalytic allylboron additions to aldimines are presented for which small amounts of Zn(OMe) 2 serve as the co‐catalyst to accelerate allyl exchange and 1,3‐borotropic shift processes. Low‐yielding and moderately α‐ and diastereoselective reactions are thus turned into highly efficient γ‐, diastereo‐, and enantioselective transformations that exhibit considerable scope.