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Dr. Youqian Deng, Prof. Dr. Chunling Fu and Prof. Dr. Shengming Ma Selectivity Manipulation of Bicyclization Reactions of 1,5-Bis(1,2-allenylketone)s: Pd versus Rh and Electronic Effect Chemistry - A European Journal 17

Version of Record online: 23 MAR 2011 | DOI: 10.1002/chem.201003546

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Select Rh! The rhodium(I)-catalyzed double cyclization of 1,5-bis(1,2-allenylketone)s gives TNF-α inhibitor (A)-type skeletons at room temperature in acetone or 1,2-dichloroethane (DCE, see scheme; Ts=Tosyl). Compared with [PdCl2(MeCN)2], [RhCl(CO)2]2 shows excellent selectivity towards the nonaromatic C[DOUBLE BOND]C bond. The selectivity of unsymmetrical substrates can be controlled by the electronic effect.

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