Stereochemical studies of type-II intramolecular ene reactions of. delta.,. epsilon.-unsaturated aldehydes

MI Johnston, JA Kwass, RB Beal…

Index: Johnston, Madeline I.; Kwass, Jill A.; Beal, Richard B.; Snider, Barry B. Journal of Organic Chemistry, 1987 , vol. 52, # 24 p. 5419 - 5424

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Citation Number: 29

Abstract

Intramolecular Lewis acid catalyzed ene reaction of aldehyde 3 gives the (E)-ene adduct 18 with 85-90% selectivity. Intramolecular ene reactions of aldehydes 6, 10, and 13 proceed with 88-100% selectivity for the isomer with an equatorial methyl group and an axial hydroxyl group. Intramolecular type-I1 ene reaction of allenic aldehyde 17 occurs either thermally or with Lewis acid catalysis to give a mixture of the expected ene adduct, bis ...