Gold-catalysis represents an interesting tool for organic chemistry, for instance gold catalysts efficiently activate alkynes for nucleophilic attack.1 In the last decade many examples of intermolecular and intramolecular hydroalkoxylations of alkynes have been reported in the literature.We now found that diyne-diols with a suitable distance between the reactive groups react by a sequence of highly selective hydroxylation or hydroaminations to deliver interesting rigid tricyclic products.2 These tricyclic compounds are the kinetic products of the reaction and can be further converted to unsaturated oxabicycloketones under more forcing conditions. Based on this observation we finally could design a one-pot synthesis, which delivers good yields of these products. As catalysts a class of newly developed carbene ligands is used.3  1. a) Hashmi, A. S. K. Chem. Rev. 2007 , 107, 3180; b) D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008 , 108, 3351.2. Hashmi, A. S. K.; B�hrle, M.; W�lfle, M; Rudolph, M.; Wieteck, M.; Rominger, F.; Frey, W. Chem. Eur. J. 2010 , 16, 9846.3. Hashmi; A. S. K.; Hengst, T.; Lothsch�tz, C.; Rominger, F. Adv. Synth. Catal. 2010 , 352, 1315.

Gold-catalyzed one-pot formation of oxabicycloketones from diyne-diols

244th National Meeting (2012)

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