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Lewis Acid Activated AzaDiels–Alder Reaction of N3Pyridylaldimines: An Experimental and Computational Study

Authors :
Palacios, Francisco
Alonso, Concepción
Arrieta, Ana
Cossío, Fernando P.
Ezpeleta, Jose M.
Fuertes, María
Rubiales, Gloria
Source :
European Journal of Organic Chemistry; April 2010, Vol. 2010 Issue: 11 p2091-2099, 9p
Publication Year :
2010

Abstract

A combined theoretical and experimental study of a Povarovtype cycloaddition reaction suggests an asynchronous concerted process that is favored by double Lewis acid activation with BF3·Et2O; endoselectivity was observed in the reactions between N3pyridylaldimines and styrene, cyclopentadiene, or indene, and substituted tetrahydro1,5naphthyridine derivatives were obtained in a regio and stereoselective fashion.

Details

Language :
English
ISSN :
1434193X and 10990690
Volume :
2010
Issue :
11
Database :
Supplemental Index
Journal :
European Journal of Organic Chemistry
Publication Type :
Periodical
Accession number :
ejs21002489
Full Text :
https://doi.org/10.1002/ejoc.200901325