Alkylaluminum halide induced cyclization of unsaturated carbonyl compounds

BB Snider, M Karras, RT Price…

Index: Snider, Barry B.; Karras, Michael; Price, Robert T.; Rodini, David J. Journal of Organic Chemistry, 1982 , vol. 47, # 23 p. 4538 - 4545

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Citation Number: 56

Abstract

2, 6-Dimethyl-5-heptenal (3) and 5-octenal (24) undergo concerted ene reactions with 1 equiv of MezAICl and cation-olefin cyclizations with 2 equiv of MezAIC1, MeAlCl,, or EtAlCl, to give a zwitterion which reacts to give several products including an ene adduct. 3, 7- Dimethyl-6-octenal (l2) and (2)-and (E)-6-nonenal (18 and 19) undergo only ene reactions with all catalysts. The enones 31 and 32 formed by reaction of 3 and 12 with ...