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Enantioselective Hydrogenation with Racemic and Enantiopure Binap in the Presence of a Chiral Ionic Liquid
Author(s) -
Chen Dianjun,
Schmitkamp Mike,
Franciò Giancarlo,
Klankermayer Jürgen,
Leitner Walter
Publication year - 2008
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.200801995
Subject(s) - enantiopure drug , binap , enantioselective synthesis , diastereomer , chemistry , moiety , chiral ligand , asymmetric hydrogenation , ionic liquid , organic chemistry , stereochemistry , medicinal chemistry , catalysis
Racemic but enantioselective : rac ‐Binap and a chiral ionic liquid (cIL) used for the asymmetric hydrogenation of dimethyl itaconate led to identical ee values as enantiopure binap. The enantiodifferentiation results primarily from a diastereomeric interaction of the binap–Rh unit and the proline ester moiety. For other substrates, enhanced enantioselectivity with inverted absolute configuration was obtained with the enantiopure ligand in the cIL relative to organic solvents.