exo-Selective Asymmetric Diels−Alder Reaction Catalyzed by Diamine Salts as Organocatalysts

Author:

Kano Taichi1,Tanaka Youhei1,Maruoka Keiji1

Affiliation:

1. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Reference11 articles.

1. For recent reviews of enantioselective Diels−Alder reactions:  (a) Evans, D. A.; Johnson, J. S. InComprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer:  New York, 1999; Vol. 3, p 1177. (b) Oppolzer, W. InComprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press:  New York, 1991; Vol. 5. (c) Kagan, H. B.; Riant, O.Chem. Rev.1992,92, 1007. (d) Diaz, L. C.J. Braz. Chem. Soc.1997,8, 289. (e) Corey, E. J.Angew. Chem., Int. Ed.2002,41, 1650. (f) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G.Angew. Chem., Int.Ed.2002,41, 1668.

2. Exo-Selective Diels-Alder Reaction Based on a Molecular Recognition Approach

3. New Strategies for Organic Catalysis:  The First Highly Enantioselective Organocatalytic Diels−Alder Reaction

4. [(Indenyl)Ru(biphop-F)]+: A Lewis Acid Catalyst That Controls both the Diene and the Dienophile Facial Selectivity in Diels–Alder Reactions This work was supported by the Swiss National Science Foundation (FNS grant 20-59374.99) and The Ministère des Affaires Etrangères from France (Lavoisier grant to V.A.). biphop-F=1,2-bis[bis(pentafluorophenyl)phosphanyloxy]-1,2-diphenylethane.

5. Iminium ion catalysis: Use of the α-effect in the acceleration of the Diels–Alder reactionElectronic supplementary information (ESI) available: 1H NMR, 13C NMR, IR and MS spectra. See http://www.rsc.org/suppdata/cc/b2/b212239a/

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