Tetrahedron

1, 5-Dicarbonyl compounds: A general preparation method

P Duhamel, L Hennequin, JM Poirier, G Tavel…

Index: Duhamel, P.; Hennequin, L.; Poirier, J. M.; Tavel, G.; Vottero, C. Tetrahedron, 1986 , vol. 42, # 17 p. 4777 - 4786

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Citation Number: 53

Abstract

In this report, a general method for the preparation of 1, 5-dicarbonyl compounds and six membered ring annelation is described. This method involves the reaction of hemiacetal vinylogs 1 with enol ethers 2 or 3 in the presence of a Lewis acid. This reaction was successfully applied to the enol ethers of α and α, α'-hindered ketones such as 2, 2, 6- trimethyl cyclohexanone. α-Cyperone and 6-epi-α-cyperone were obtained using this ...

~66%

~39%

~50%

~36%

~46%

~47%

~45%

~70%

~71%

~79%

~19%

~73%

~29%

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[Heathcock, Clayton H.; Mahaim, Cyril; Schlecht, Matthew F.; Utawanit, Thanin Journal of Organic Chemistry, 1984 , vol. 49, # 18 p. 3264 - 3274]