Concepedia

Alkenyl C−H Insertion of Iodonium Ylides into Pyrroles:  Studies toward the Total Syntheses of Tolmetin and Amtolmetin Guacil

Christina Batsila, Efstathios P. Gogonas, George E. Κostakis, Lazaros P. Hadjiarapoglou

Organic Letters · 2003 · 49 citations · 16 references

DOI

Concepts

Abstract

The thermal-catalyzed or photochemical reaction of iodonium ylides with pyrroles yields exclusively alpha-substituted pyrroles in moderate to good yields. [reaction: see text]

References

16

Regioselective synthesis of acylpyrroles

Masatoshi Kakushima, Pierre Hamel, Richard Frenette et al. · The Journal of Organic Chemistry · 1983 · 200 citations

, , +6

Carbenoid chemistry. Reaction of pyrrole derivatives with ethyl diazoacetate

Bruce E. Maryanoff · The Journal of Organic Chemistry · 1979 · 66 citations

, , +6

Phenyliodonium bis(phenylsulfonyl)methylide, a new hypervalent iodonium ylide

Lazaros P. Hadjiarapoglou, Spyros Spyroudis, A. VARVOGLIS · Journal of the American Chemical Society · 1985 · 63 citations

, , +4

Radical-based syntheses of 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid (ketorolac)

Dean R. Artis, In-Seop Cho, Joseph M. Muchowski · Canadian Journal of Chemistry · 1992 · 62 citations

, , +11

Metal‐catalyzed carbenoid reactions with iodonium and sulfonium ylides

Paul Müller, Daniel Fernández, Patrice Nury et al. · Journal of Physical Organic Chemistry · 1998 · 61 citations

, , +12