ChemInform Abstract: Cu‐Catalyzed Cascades to Carbocycles: Union of Diaryliodonium Salts with Alkenes or Alkynes Exploiting Remote Carbocations.

Abstract

The reaction of alkyl instead of aryl substituted alkynes with (II) under the investigated conditions does not give the corresponding alkyl substituted cyclopentenes. The conversion of an enantiomerically enriched aryl alkyne proceeds with minimal erosion of the enantiomeric excess. Compound (XIX) is further transformed to the retinoid receptor agonist BMS-189453 (XX) offering a significantly shorter synthetic route to this drug compared to previously developed ways. -(ZHANG, F.; DAS, S.; WALKINSHAW, A. J.; CASITAS, A.; TAYLOR, M.; SUERO, M. G.; GAUNT*, M. J.; J. Am. Chem. Soc. 136 (2014) 25, 8851-8854, http://dx.