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Catalytic Asymmetric Synthesis of N‐Chiral Amine Oxides
Author(s) -
Bhadra Sukalyan,
Yamamoto Hisashi
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.201606354
Subject(s) - stereocenter , kinetic resolution , amine gas treating , bimetallic strip , catalysis , chemistry , combinatorial chemistry , titanium , enantioselective synthesis , organic chemistry
Direct asymmetric synthesis of N ‐chiral amine oxides was accomplished (up to 91:9 e.r.) by means of a bimetallic titanium catalyst. A hydroxy group situated at the γ‐position of the N stereocenter enables the desired N‐oxidation through dynamic kinetic resolution of the trivalent amine substrates. The method was further extended to the kinetic resolution of racemic γ‐amino alcohols with a preexisting stereocenter, giving an important class of enantioenriched (up to 99.9:0.1 e.r.) building blocks that are otherwise difficult to synthesize.