Lewis Acid Activated Aza‐Diels–Alder Reaction of  N ‐(3‐Pyridyl)aldimines: An Experimental and Computational Study | Zendy

Palacios Francisco | Zendy; Alonso Concepción | Zendy; Arrieta Ana | Zendy; Cossío Fernando P. | Zendy; Ezpeleta Jose M. | Zendy; Fuertes María | Zendy; Rubiales Gloria | Zendy

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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.

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