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Enantioselective Rhodium‐Catalyzed Synthesis of Branched Allylic Amines by Intermolecular Hydroamination of Terminal Allenes
Author(s) -
Cooke Michael L.,
Xu Kun,
Breit Bernhard
Publication year - 2012
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.201206594
Subject(s) - hydroamination , enantioselective synthesis , allylic rearrangement , rhodium , allene , chemistry , regioselectivity , catalysis , organic chemistry , combinatorial chemistry , medicinal chemistry
Branching out : The rhodium‐catalyzed enantioselective hydroamination of monosubstituted allenes with anilines permits the atom‐economic synthesis of valuable branched allylic amines. In contrast to previous linear selective allene hydroaminations, a Rh I /Josiphos catalyst system (see scheme; cod=1,5‐cyclooctadiene, DCE=1,2‐dichloroethane) allows branched allylic amines to be obtained with perfect regioselectivity, high yield, and good enantioselectivity.