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1,3-Dipolar Cycloaddition of N-Substituted Dipolarophiles and Nitrones: Highly Efficient Solvent-Free Reaction.

Authors :
Binh Nguyen, Thanh
Martel, Arnaud
Dhal, Robert
Dujardin, Gilles
Source :
Journal of Organic Chemistry. 4/4/2008, Vol. 73 Issue 7, p2621-2632. 12p. 6 Charts, 3 Graphs.
Publication Year :
2008

Abstract

New isoxazolidines were synthesized in good to excellent yields by I ,3-dipolar cycloaddition of N-vinylamide dipolarophiles and nitrones. Strikingly, solvent-free conditions gave high conversion and yields, shortened reaction time, and minimized degradation products. N-Vinyloxazolidin-2-one and its analogues used in these cycloaddition reactions were conveniently prepared in excellent yields by a modified version of Buchwald's one-step copper-catalyzed vinylation using vinyl bromide. From the adducts, a two-step access to various unsymmetric aspartate derivatives was also described. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00223263
Volume :
73
Issue :
7
Database :
Academic Search Index
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
31830589
Full Text :
https://doi.org/10.1021/jo702490w