Abstract
AbstractThe synthesis of the cyclic enamino ketones 1–3 bearing an alkylthio or an phenylthio group and their reactivity in hetero Diels‐Alder reactions with enol ethers is described. Only compound 3 with an phenylthio group undergoes a cycloaddition with 16a–d to afford the diastereomeric adducts 17a–d and 18a–d. To estimate the activation by a phenylthio and alkylthio group semiempirical PM3/RHF calculations of the frontier orbital energies and coefficients of different enamine carbaldehydes have been performed.
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