Synthesis of optically active 5, 6, 7, 8??tetrahydroquinolines

F Soccolini, G Chelucci…

Index: Soccolini, F.; Chelucci, G.; Botteghi, C. Journal of Heterocyclic Chemistry, 1984 , vol. 21, p. 1001 - 1004

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Citation Number: 3

Abstract

Abstract (+)-(R)-5-Methyl-and (+)-(R)-2, 5-dimethyl-8-isopropylidene-5, 6-dihydro-7H- quinoline, 7 and 11, were synthesized by reaction of (R)-pulegon morpholino-enamine with acrolein or methyl vinyl ketone. The Michael adducts thus formed were reacted with hydroxylammonium hydrochloride in polar media. Compound 7 was also obtained by thermal rearrangement of the O-allyl ether of pulegone oxime. The selectivity of both ...