The development of the rhodium-catalyzed [(3+2)+1] carbocyclization reaction of alkynylidenecyclopropanes with carbon monoxide to construct polysubstituted phenols is described. This work offers a convenient method for the selective formation of tetra- and pentasubstituted phenols, which provide important intermediates for target directed synthesis. Finally, the ability to regiospecifically functionalize the phenols using conventional methods further illustrates the utility of this process.
A rhodium-catalyzed carbocyclization reaction of alkynylidenecyclopropanes with carbon monoxide to prepare bicyclohexa-2,5-dienones is described. This protocol offers convenient access to doubly conjugated cyclic enones and is tolerant of functionalized alkynes and cyclopropanes. Furthermore, a photochemical rearrangement of a bicyclohexa-2,5-dienone facilitates the construction of a highly functionalized bicyclopentenone containing two contiguous stereogenic centres, which represents a versatile intermediate for target directed synthesis.
The title process allows the conversion of 1,6-enynes into heterocarbo-5,6-bicyclic systems. The reaction of substrate (VI) gives the regioisomer (VII) as the sole product. -(EVANS*, P. A.; BURNIE, A. J.; NEGRU, D. E.; Org. Lett. 16 (2014) 17, 4356-4359, http://dx.doi.org/10.1021/ol501724s ; Dep. Chem., Queen's Univ., Kingston, Ont. K7L 3N6, Can.; Eng.) -Mais 09-088
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