Helvetica chimica acta

Facile Hetero??Diels??Alder Reaction of α, β??Unsaturated Acyl Cyanides and Enol Ethers: Syntheses of 2??Alkoxy??3, 4??dihydro??2H??Pyran??6??carbonitriles

RA John, V Schmid, H Wyler

Index: John, Robert A.; Schmid, Vincent; Wyler, Hugo Helvetica Chimica Acta, 1987 , vol. 70, p. 600 - 606

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Citation Number: 20

Abstract

1. Introduction. - The reaction of a,/3 -unsaturated carbonyl compounds with alkyl vinyl ethers, a classical example of a Die1.r-Alder cycloaddition of inverse electron demand [I], makes available various derivatives of 2-alkoxy-3,4-dihydro-2H-pyrans useful in the synthesis of carbohydrates [2], thromboxanes [3], and spiroacetals [4]. When elevated temperature is used for this reaction, the theoretically favoured 'endo ' adducts are not the exclusive products. ...