Stereochemical studies on the intramolecular imino Diels-Alder reaction

B Nader, TR Bailey, RW Franck…

Index: Nader,B.; Bailey,T.R.; Franck,R.W. Journal of the American Chemical Society, 1981 , vol. 103, p. 7573

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Citation Number: 32

Abstract

Abstract: The intramolecular Diels-Alder cycloaddition of some N-acylimines has been shown to be a totally stereoselective process producing tetrahydropyridine systems having a trans relationship of hydrogens CY to nitrogen. Thus, thermolysis of 13 or 14 led to a 55: 45 mixture of trans-6, 5-fused cycloadducts 16 and 17, respectively. The stereostructures of these compounds were established by direct correlation with authentic methyl ...