Rhodium(III)‐Catalyzed Alkenyl CH Bond Functionalization: Convergent Synthesis of Furans and Pyrroles

Yajing Lian, Tatjana Huber, Kevin D. Hesp, Robert G. Bergman, Jonathan A. Ellman

Angewandte Chemie International Edition · 2012 · 177 citations · 65 references

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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.

References

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