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Chiral Nanoparticles/Lewis Acids as Cooperative Catalysts for Asymmetric 1,4‐Addition of Arylboronic Acids to α,β‐Unsaturated Amides
Author(s) -
Yasukawa Tomohiro,
Saito Yuuki,
Miyamura Hiroyuki,
Kobayashi Shū
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.201601559
Subject(s) - catalysis , chemistry , amide , reactivity (psychology) , lewis acids and bases , nanoparticle , addition reaction , organic chemistry , combinatorial chemistry , amino acid , nanotechnology , materials science , biochemistry , medicine , alternative medicine , pathology
Abstract Cooperative catalysts consisting of chiral Rh/Ag nanoparticles and Sc(OTf) 3 have been developed that catalyze asymmetric 1,4‐addition reactions of arylboronic acids with α,β‐unsaturated amides efficiently. The reaction has been considered one of the most challenging reactions because of the low reactivity of the amide substrates. The new catalysts provide the desired products with outstanding enantioselectivities (>98 % ee ) in the presence of low loadings (<0.5 mol %) of the catalyst.