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Highly Enantioselective Hydrogenation of Cyclic Enol Acetates Catalyzed by a Rh–PennPhos Complex
Author(s) -
Jiang Qiongzhong,
Xiao Dengming,
Zhang Zhaoguo,
Cao Ping,
Zhang Xumu
Publication year - 1999
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/(sici)1521-3773(19990215)38:4<516::aid-anie516>3.0.co;2-b
Subject(s) - enantioselective synthesis , rhodium , asymmetric hydrogenation , enol , catalysis , chemistry , substrate (aquarium) , ligand (biochemistry) , stereochemistry , organic chemistry , medicinal chemistry , receptor , biochemistry , oceanography , geology
The electron‐rich and conformationally rigid ( R , S , R , S )‐Me‐PennPhos ligand (shown schematically) appears to chelate rhodium and form well‐defined chiral pockets. This allows, for example, efficient differentiation between the two enantiotopic approaches available to a substrate in a hydrogenation reaction. The Rh–Me‐PennPhos complex is the first catalyst for the highly enantioselective asymmetric hydrogenation of cyclic enol acetates. For example, 3,4‐dihydronaphth‐1‐yl acetate can be hydrogenated with up to 99% ee .