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Stereochemical studies of type-II intramolecular ene reactions of .delta.,.epsilon.-unsaturated aldehydes
Journal article   Peer reviewed

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

Madeline I Johnston, Jill A Kwass, Richard B Beal and Barry B Snider
Journal of organic chemistry, Vol.52(24), pp.5419-5424
11/01/1987

Abstract

Catalysis Ene reactions Aldehydes Lewis acid catalysis Chemical Reactions Molecular Chemistry Organic Chemistry
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-II ene reaction of allenic aldehyde 17 occurs either thermally or with Lewis acid catalysis to give a mixture of the expected ene adduct, bis exocyclic diene 26, and diene 27.

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