M.S.M. thanks the Alexander von Humboldt Foundation, and H.B.K. thanks The Council of Higher Education of Turkey for a fellowship.
Asymmetric Brønsted Acid Catalyzed Cycloadditions—Efficient Enantioselective Synthesis of Pyrazolidines, Pyrazolines, and 1,3-Diamines from N-Acyl Hyrazones and Alkenes†
Article first published online: 19 NOV 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 51, pages 12864–12868, December 14, 2012
How to Cite
Rueping, M., Maji, M. S., Küçük, H. B. and Atodiresei, I. (2012), Asymmetric Brønsted Acid Catalyzed Cycloadditions—Efficient Enantioselective Synthesis of Pyrazolidines, Pyrazolines, and 1,3-Diamines from N-Acyl Hyrazones and Alkenes . Angew. Chem. Int. Ed., 51: 12864–12868. doi: 10.1002/anie.201205813
- Issue published online: 10 DEC 2012
- Article first published online: 19 NOV 2012
- Manuscript Received: 23 JUL 2012
- Alexander von Humboldt Foundation
- homogeneous catalysis;
- hydrogen bonding;
- ion pairs
A general, metal-free, highly enantioselective Brønsted acid catalyzed [3+2] cycloaddition between hydrazones and alkenes has been developed that affords pyrazolidine derivatives (see scheme). The resulting optically active pyrazolidines can undergo many chemical transformations which allow, for example, the enantioselective synthesis of valuable pyrazolines and 1,3-diamines.