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Asymmetric Hydrogenation of Azaindoles: Chemo‐ and Enantioselective Reduction of Fused Aromatic Ring Systems Consisting of Two Heteroarenes
Author(s) -
Makida Yusuke,
Saita Masahiro,
Kuramoto Takahiro,
Ishizuka Kentaro,
Kuwano Ryoichi
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.201606083
Subject(s) - enantioselective synthesis , ring (chemistry) , chelation , phosphine , asymmetric hydrogenation , chemistry , enantiomer , ligand (biochemistry) , catalysis , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , receptor
High enantioselectivity was achieved for the hydrogenation of azaindoles by using the chiral catalyst, which was prepared from [Ru(η 3 ‐methallyl) 2 (cod)] and a trans ‐chelating bis(phosphine) ligand (PhTRAP). The dearomative reaction exclusively occurred on the five‐membered ring, thus giving the corresponding azaindolines with up to 97:3 enantiomer ratio.