An Entry to a Chiral Dihydropyrazole Scaffold: Enantioselective [3 + 2] Cycloaddition of Nitrile Imines
- 18 May 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (23) , 8276-8277
- https://doi.org/10.1021/ja051650b
Abstract
We have developed a versatile strategy to access dihydropyrazoles in highly enantioenriched form. Dipolar cycloaddition of electron-deficient acceptors and in situ-generated nitrile imines proceeds with high regio- and enantioselectivity using 10 mol % chiral Lewis acid catalyst. A variety of dihydropyrazoles that incorporate functionality for further manipulation have been prepared.Keywords
This publication has 6 references indexed in Scilit:
- Enantioselective Radical Addition/Trapping Reactions with α,β-Disubstituted Unsaturated Imides. Synthesis ofanti-Propionate AldolsJournal of the American Chemical Society, 2005
- 4,5-Dihydro-1H-pyrazole Derivatives with Inhibitory nNOS Activity in Rat Brain: Synthesis and Structure−Activity RelationshipsJournal of Medicinal Chemistry, 2004
- Versatile, Diastereoselective Additions of Silyl Ketene Acetals, Allyl Tributylstannane, and Me3SiCN to N-Acyl Pyrazolines: Asymmetric Synthesis of Densely Functionalized PyrazolidinesOrganic Letters, 2000
- Lewis Acid-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions of Diazoalkane: Chiral Ligand/Achiral Auxiliary Cooperative Chirality ControlJournal of the American Chemical Society, 2000
- Geometries of nitrilium betaines. The clarification of apparently anomalous reactions of 1,3-dipolesJournal of the American Chemical Society, 1976
- Origin of reactivity, regioselectivity, and periselectivity in 1,3-dipolar cycloadditionsJournal of the American Chemical Society, 1973