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( R )‐Binap‐Mediated Asymmetric Hydrogenation with a Rhodacarborane Catalyst in Ionic‐Liquid Media
Author(s) -
Yinghuai Zhu,
Carpenter Keith,
Bun Ching Chi,
Bahnmueller Stefan,
Ke Chan Pek,
Srid Venugopal Shanmugham,
Kee Leong Weng,
Hawthorne M. Frederick
Publication year - 2003
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.200351273
Subject(s) - ionic liquid , catalysis , binap , asymmetric hydrogenation , chemistry , enantioselective synthesis , aryl , organic chemistry , medicinal chemistry , alkyl
Unsymmetrical aryl ketones undergo asymmetric hydrogenation in ionic‐liquid media in the presence of ( R )‐binap and a rhodacarborane catalyst derived from the suicide precursor 1 (see scheme). Ketones that are poor substrates for other methods can be hydrogenated in quantitative yields with very high enantioselectivities (97.3–99.5 % ee ). The novel ionic liquid ( N‐n ‐butylpyridinium) + ( closo ‐CB 11 H 12 ) − provides a superior medium for these reactions.