Ernst Schering Foundation Symposium Proceedings, Vol. 2, pp. 207–253
DOI 10.1007/2789_2008_085
© Springer-Verlag Berlin Heidelberg
Published Online: 30 April 2008
New Developments in Enantioselective
Brønsted Acid Catalysis: Chiral Ion Pair
Catalysis and Beyond
M. Rueping
(u) , E. Sugiono
Degussa Endowed Professorship, Institute of Organic Chemistry and Chemical Biology,
Johann Wolfgang Goethe-Universität Frankfurt am Main, Max-von-Laue Strasse 7,
60438 Frankfurt am Main, Germany
email: M.rueping@chemie.uni-frankfurt.de
1
Development of the First Highly Enantioselective Organocatalytic
Reduction of Ketimines . . . . . . . . . . . . . . . . . . . . . . . 209
2
Biomimetic Reductions: Amino Acid Dehydrogenases as the Role
Model for the Brønsted Acid Catalyzed Transfer Hydrogenation
of Ketimines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 209
3
The First Enantioselective Brønsted Acid Catalyzed Transfer
Hydrogenation of Ketimines: Chiral Phosphates Are Efficient
Metal-Free Catalysts . . . . . . . . . . . . . . . . . . . . . . . . . 213
4
Highly Enantioselective Brønsted Acid Catalyzed Transfer
Hydrogenation of Quinolines: Development
of a New Organocatalytic Cascade Reaction . . . . . . . . . . . . 216
5
Enantioselective Reduction of Benzoxazines, Benzthiazines,
and Benzoxazinones: Remarkably Low Catalyst Loading
in the Asymmetric Brønsted Acid Catalyzed
Transferhydrogenation . . . . . . . . . . . . . . . . . . . . . . . . 221
6
First Organocatalytic Enantioselective Reduction of Pyridines . . . 225
7
First Highly Enantioselective Brønsted Acid Catalyzed
Strecker Reaction: Use of C-Nucleophiles
in Chiral Ion Pair Catalysis . . . . . . . . . . . . . . . . . . . . . 230
8
Asymmetric Brønsted Acid Catalyzed Imino-Azaenamine
Reaction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 233