Peter R. Schreiner
Organocatalysis combines the concepts of molecular recognition and supramolecular chemistry with enzyme-like catalytic concepts; this branch of research may therefore be coined with the notion of “the hunt for the smallest enzyme.”1 Noting that about half of all enzymes do not carry a metal center it is obvious that this approach has long been underappreciated. Although organocatalysis as such is a new field, it is already possible to catalyze many types of organic reactions with small, well-designed organic molecules. This circumvents the use of often toxic metals, and the preparation of the catalysts is much easier as it relies on the well-developed synthetic arsenal for tailor-making organic structures. While many approaches rely on covalent attachment of the catalyst (e.g., proline catalysis), we focus entirely on non-covalently bound catalysts;2 the talk will emphasize the notion of noncovalent bonding that is in line with Pauling’s paradigms of enzyme activity. In our group we have developed hydrogen-bonding thiourea-based catalysts that are effective in catalyzing Diels-Alder reactions,2 acid-free acetalizations,3 epoxide openings,4 and other reactions. Many other groups have not picked up this catalytic principle and apply it to a manifold of fascinating reactions.
- Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289-296.
- Wittkopp, A.; Schreiner, P. R. In The Chemistry of Dienes and Polyenes; Rappoport, Z., Ed.; John Wiley & Sons: Chichester, 2000; Vol. 2, pp 1029-1088; Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217-220; Wittkopp, A.; Schreiner, P. R. Chem. Eur. J. 2003, 9, 407-414.
- Kotke, M.; Schreiner, P. R. Tetrahedron 2005, in print.
- Kleiner, C.; Schreiner, P. R., in preparation.
- Schreiner, P. R.; Fokin, A. A.; Lauenstein, O.; Okamoto, Y.; Wakita, T.; Rinderspacher, C.; Robinson, G. H.; Vohs, J. K.; Campana, C. F. J. Am. Chem. Soc. 2002, 124, 13348-13349; Schreiner, P. R.; Lauenstein, O.; Butova, E. D.; Gunchenko, P. A.; Kolomitsin, I. V.; Wittkopp, A.; Feder, G.; Fokin, A. A. Chem. Eur. J. 2001, 7, 4996–5003; Fokin, A. A.; Lauenstein, O.; Gunchenko, P. A.; Schreiner, P. R. J. Am. Chem. Soc. 2001, 123, 1842-1847; Lauenstein, O.; Fokin, A. A.; Schreiner, P. R. Org. Lett. 2000, 2, 2201-2204; Schreiner, P. R.; Lauenstein, O.; Butova, E. D.; Fokin, A. A. Angew. Chem. Int. Ed. Engl. 1999, 38, 2786-2788; Schreiner, P. R.; Lauenstein, O.; Kolomitsyn, I. V.; Nadi, S.; Fokin, A. A. Angew. Chem. Int. Ed. Engl. 1998, 37, 1895-1897.