Lewis Acid Activated Aza‐Diels–Alder Reaction of <i>N</i>‐(3‐Pyridyl)aldimines: An Experimental and Computational Study

Francisco Palácios, Concepción Alonso, Ana Arrieta, Fernando P. Cossío, J.M. Ezpeleta, Marı́a Fuertes, Gloria Rubiales

European Journal of Organic Chemistry · 2010 · 56 citations · 39 references

Concepts

Abstract

Abstract 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.

References

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