One‐Pot Stereoselective Synthesis of 2‐Acylaziridines and 2‐Acylpyrrolidines from N‐(Propargylic)hydroxylamines
Authors:
- 1 February 2013
- journal article
- research article
- Published by Wiley in Chemistry – An Asian Journal
- Vol. 8 (4) , 824-831
Abstract
The stereoselective direct transformation of N‐(propargylic)hydroxylamines into cis‐2‐acylaziridines was achieved by the combined use of AgBF4 and CuCl. Copper salts were found to promote the transformation of the intermediary 4‐isoxazolines into 2‐acylaziridines and both 3‐aryl‐ and 3‐alkyl‐substituted 2‐acylaziridines could be prepared by using this method. Furthermore, subsequent 1,3‐dipolar cycloaddition of azomethine ylides that were generated in situ from the intermediary 2‐acylaziridines with maleimides was achieved in a stereoselective one‐pot procedure to afford the corresponding 2‐acylpyrrolidines, which consisted of an octahydropyrrolo[3,4‐c]pyrrole skeleton.Keywords
This publication has 63 references indexed in Scilit:
- Highly Stereoselective Samarium(II) Iodide-Mediated Aldol Reactions of Acylaziridines with AldehydesBulletin of the Chemical Society of Japan, 2005
- Access to Isolable Azomethine Ylides by Photochemical Transformation of 2,3‐DihydroisoxazolesEuropean Journal of Organic Chemistry, 2003
- Efficient Entry to Highly Functionalized β-Lactams by Regio- and Stereoselective 1,3-Dipolar Cycloaddition Reaction of 2-Azetidinone-Tethered Nitrones. Synthetic ApplicationsThe Journal of Organic Chemistry, 2002
- Regio- and Stereoselectivity of Cycloadditions of Trifluoromethylated Azomethine YlideBulletin of the Chemical Society of Japan, 1994
- A comparison of 4-oxazoline and 2-acylaziridine routes to azomethine ylidesThe Journal of Organic Chemistry, 1988
- Applications of the fluorinated 1,3-dipolar compounds as the building blocks of the heterocycles with fluorine groups. Part XII. Synthesis of trifluoromethylisoxazolines and their rearrangement into trifluoromethylaziridines [1]Journal of Fluorine Chemistry, 1988
- Isoxazoles. XXIII. Synthesis of N-Substituted 4-Isoxazolines and Their Conversion into 2-AcylaziridinesChemical and Pharmaceutical Bulletin, 1974
- Thermal Decomposition of Stereoisomeric 3-Aroyl- and 3-Carbomethoxyaziridines in AcetonitrileCanadian Journal of Chemistry, 1972
- Nuclear magnetic resonance spectra and nitrogen inversion in 1-alkyl-2-aryl-3-carboaziridinesThe Journal of Organic Chemistry, 1971
- Ethylene Imine KetonesJournal of the American Chemical Society, 1945