Ernst Schering Foundation Symposium Proceedings, Vol. 2, pp. 141–158
DOI 10.1007/2789_2008_082
© Springer-Verlag Berlin Heidelberg
Published Online: 30 April 2008
Asymmetric Organocatalysis
on a Technical Scale: Current Status
and Future Challenges
H. Gröger
(u)
Department of Chemistry and Pharmacy, University of Erlangen-Nuremberg,
Henkestr. 42, 91054 Erlangen, Germany
email: harald.groeger@chemie.uni-erlangen.de
1
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 141
2
Industrially Relevant Advantages of Organocatalysis . . . . . . . . 142
3
Organocatalytic Transformations of Industrial Relevance . . . . . 143
3.1
Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 143
3.2
Intramolecular Aldol Reaction:
Hajos–Parrish–Eder–Wiechert–Sauer Reaction . . . . . . . . . . . 144
3.3
Alkylation of Cyclic Ketones . . . . . . . . . . . . . . . . . . . . 145
3.4
Alkylation of Glycinates for the Synthesis
of Optically Active α-Amino Acids . . . . . . . . . . . . . . . . . 146
3.5
Strecker Reaction . . . . . . . . . . . . . . . . . . . . . . . . . . 149
3.6
Epoxidation/I: Julia–Colonna–Type Epoxidation . . . . . . . . . . 150
3.7
Epoxidation/II: Shi Epoxidation . . . . . . . . . . . . . . . . . . . 153
3.8
Other Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . 153
4
Conclusion and Outlook . . . . . . . . . . . . . . . . . . . . . . . 154
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 155
1
Introduction
The development of methodologies for the production of chiral building
blocks is of crucial importance, as such enantiomerically pure molecules
are required as key intermediates in the synthesis of drugs. Due to the