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Synthesis 1997; 1997(6): 628-630
DOI: 10.1055/s-1997-1395
short paper
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Cycloaddition Reactions of (Z)-β-Siloxyacrylonitriles with Enones: Synthesis of 4H-Pyrans and Dihydro-2H-pyrans

Asunción Barbero, Carlos García, Begoña González, Francisco J. Pulido* , Juan A. Rincon
  • *Departamento de Química Orgánica, Universidad de Valladolid, E-47011 Valladolid, Spain, Fax +34(83)423013
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Publication Date:
31 December 2000 (online)

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Reaction of (Z)-β-siloxyacrylonitriles 1 with enones 2 afforded 4H-pyrans 3 and dihydro-2H-pyrans 4 regio- and stereoselectively. A concerted hetero-Diels-Alder process is proposed.

cycloaddition - silyl enol ether - enone - isoxazole - pyrans