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Keywords:

  • allenes;
  • cyclization;
  • furans;
  • palladium;
  • rhodium
Thumbnail image of graphical abstract

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.