| Abstract
| - Readily available N-acyl-5-vinyl-2,3-dihydro-4-pyridones undergo Diels−Alder cyclization withvarious dienophiles to afford novel octahydroquinolines containing synthetically useful functionality.With dihydropyridone 5 and cis-disubstituted dienophiles, the resulting cycloadducts were obtainedas single diastereomers in good to excellent yield. The corresponding reaction of 5 with methylacrylate, acrylonitrile, and phenyl vinyl sulfone showed modest preference for the endo adducts.The effect of the dihydropyridone C-2 and C-4 substituents on the degree of diastereofacial controlwas examined. By using this methodology, the core decahydroquinoline skeleton of gephyrotoxinwas prepared in a stereocontrolled fashion. Interesting reactivity was observed with certaindienophiles leading to ring-opening of the initially formed cycloadducts. This tandem reactionprovides a route to uniquely substituted β-aminoketones, alcohols, and unnatural amino acids.
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