Heterocyclic Compounds
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ChemInform Abstract: 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.
First published: September 1, 1987
Abstract
The reaction of (I) or the nitrile generated in situ from (IV) with enol ethers (II) or (VII) proceeds with high endo selectivity to yield the title compounds (III), (VI) and (VIII)/(IX).
ChemInform Abstract
The reaction of (I) or the nitrile generated in situ from (IV) with enol ethers (II) or (VII) proceeds with high endo selectivity to yield the title compounds (III), (VI) and (VIII)/(IX). As demonstrated for (IIIa), treatment with BF3 results in epimerization to give mixtures containing the trans isomers as major products. Further analogues of (IIIa) can be obtained by modification of the cyanidegroup using standard procedures.
