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Mizoroki–Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers
Author(s) -
Medina Jose M.,
Moreno Jesus,
Racine Sophie,
Du Shuaijing,
Garg Neil K.
Publication year - 2017
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.201703174
Subject(s) - stereocenter , amide , chemistry , steric effects , adduct , vicinal , catalysis , combinatorial chemistry , organic chemistry , enantioselective synthesis
We report non‐decarbonylative Mizoroki–Heck reactions of amide derivatives. The transformation relies on the use of nickel catalysis and proceeds using sterically hindered tri‐ and tetrasubstituted olefins to give products containing quaternary centers. The resulting polycyclic or spirocyclic products can be obtained in good yields. Moreover, a diastereoselective variant of this method gives access to an adduct bearing vicinal, highly substituted sp 3 stereocenters. These results demonstrate that amide derivatives can be used as building blocks for the assembly of complex scaffolds.