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Lewis Acid Activated Aza‐Diels–Alder Reaction of N ‐(3‐Pyridyl)aldimines: An Experimental and Computational Study
Author(s) -
Palacios Francisco,
Alonso Concepción,
Arrieta Ana,
Cossío Fernando P.,
Ezpeleta Jose M.,
Fuertes María,
Rubiales Gloria
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901325
Subject(s) - aldimine , chemistry , cyclopentadiene , lewis acids and bases , cycloaddition , stereoselectivity , diels–alder reaction , styrene , indene , selectivity , organic chemistry , medicinal chemistry , catalysis , copolymer , polymer
A combined theoretical and experimental study of a Povarov‐type cycloaddition reaction suggests an asynchronous concerted process that is favored by double Lewis acid activation with BF 3 · Et 2 O; endo selectivity was observed in the reactions between N ‐(3‐pyridyl)aldimines and styrene, cyclopentadiene, or indene, and substituted tetrahydro‐1,5‐naphthyridine derivatives were obtained in a regio‐ and stereoselective fashion.