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

doi:10.1055/s-1997-1395

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

Abstract

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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

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