Rhodium(III)-catalyzed alkenyl C-H bond functionalization: convergent synthesis of furans and pyrroles

Angew Chem Int Ed Engl. 2013 Jan 7;52(2):629-33. doi: 10.1002/anie.201207995. Epub 2012 Nov 22.

Abstract

Ring in the new: a new annulation for the efficient synthesis of substituted furans and pyrroles is reported. The Rh(III) -catalyzed reaction of O-methyl α,β-unsaturated oximes with aldehydes and N-tosyl imines affords secondary alcohol and amine intermediates, respectively. Cyclization and aromatization occurs under the reaction conditions to provide access to biologically relevant furans and pyrroles in good yields. Cp*=C(5)Me(5), DCE=1,2-dichloroethane, THF=tetrahydrofuran.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Furans
  • Pyrroles
  • Rhodium