Download PDF
Synfacts 2011(9): 0988-0988  
DOI: 10.1055/s-0030-1261038
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Tetrahydropyridines by an Aza-Diels-Alder Reaction

Contributor(s): Mark Lautens, Stephen G. Newman
J. Vicario, D. Aparicio, F. Palacios*
Universidad del País Vasco, Apartado, Spain
Further Information

Publication History

Publication Date:
19 August 2011 (online)

    Permissions and Reprints

Significance

Nitrogen-containing heterocycles are widespread in natural products and pharmaceuticals. The Diels-Alder reaction utilizing imines (aza-Diels-Alder) is perhaps the most direct method for accessing six-membered heterocycles (see Review below). In the present communication, the authors report on the use of 1-azadienes as dienes in the inverse-electron-demand aza-Diels-Alder reaction with enamine dienophiles.

Review: P. Buonora, J. C. Olsen, T. Oh Tetrahedron 2001, 57, 6099-6138.