Annulation of. alpha.-formyl. alpha.,. beta.-unsaturated ketones by a Michael addition-cyclization sequence. A versatile synthesis of alicyclic six-membered rings

…, MJ Brannon, CG Burgos, TE Goodwin…

Index: Meyer, Walter L.; Brannon, Michael J.; Burgos, Celmira da G.; Goodwin, Thomas E.; Howard, Ralph W. Journal of Organic Chemistry, 1985 , vol. 50, # 4 p. 438 - 447

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Citation Number: 27

Abstract

The potential generality of the annulation sequence shown in Scheme I1 (10-11-12-13- 14/15) has been examined in model systems. Dehydrogenation of a-formylcyclohexanones lla-d with 1 equiv of DDQ rapidly produces a,@-unsaturated a-formyl ketones 12a-d, even when the structures (12a, b) would permit over-oxidation to a benzenoid system. DDQ also converts 2-acetyl-4, 4-dimethylcyclohexanone to its 2, 3-dehydro derivative, but this ...

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