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Transition metal-catalyzed higher-order carbocyclization reactions provide powerful methods for the stereoselective construction of complex polycyclic systems that are generally not accessible via classical pericyclic reactions. We have demonstrated the merit of the rhodium-catalyzed [m+n+n] carbocyclization reactions of carbon and heteroatom tethered 1,6-enynes with carbon monoxide, alkynes and dienes. More recently we have explored the development of a stereoselective rhodium-catalyzed [3+2+2] carbocyclization of 1,6-alkenylidenecyclopropanes with activated alkynes for the construction of cis-fused bicycloheptadienes, which prompted the isolation of the key metallacycle intermediate and the expansion of the scope of p-fragments to carbon monoxide and allenes.[4,5] The seminar will outline some of these developments and their application to challenging bioactive natural products.
1. Inglesby, P. A.; Evans, P. A. Chem. Soc. Rev. 2010, 39, 2791.
2. (a) Evans, P. A.; Inglesby, P. A. J. Am. Chem. Soc. 2008, 130, 12838. (b) Evans, P. A.; Inglesby, P. A.; Kilbride, K. Org. Lett. 2013, 15, 1798. (c) Evans, P. A.; Negru, D. E.; Shang, D. Angew. Chem. Int. Ed. 2015, 54, 4768.
3. Inglesby, P. A.; Bacsa, J.; Negru, D. E.; Evans, P. A. Angew. Chem. Int. Ed. 2014, 53, 3952.4. Mazumder, S.; Shang, D.; Negru, D. E.; Baik, M.-H.; Evans, P. A. J. Am. Chem. Soc. 2012, 134, 20569.