Intramolecular and intermolecular Lewis acid catalyzed ene reactions using ketones as enophiles

AC Jackson, BE Goldman…

Index: Jackson, Andrew C.; Goldman, Boris E.; Snider, Barry B. Journal of Organic Chemistry, 1984 , vol. 49, # 21 p. 3988 - 3994

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Citation Number: 45

Abstract

Alkylaluminum halide catalyzed intramolecular ene reactions of 8-keto esters proceed in high yield to give cyclohexanols, via either a type I or type I1 process. Treatment of &keto ester 3 with MezAICl gives cis-fused ene adduct 5 in 67% yield. Similarly, 10 gives a 90% yield of 11 while treatment of 14 with Me3Al gives a 63% yield of 15. Treatment of 21 with MezAICl gives a 52% yield of a mixture of isomeric ene adducts 22 and 23. Treatment of ...