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Beilstein J. Org. Chem. 2011, 7, 839–846, doi:10.3762/bjoc.7.96
Graphical Abstract
Scheme 1: Gold-catalysed cycloisomerisations of aryl–alkynyl aziridine to pyrroles.
Scheme 2: Working mechanism to rationalise the formation of two regiosomeric pyrroles in the gold catalysed c...
Scheme 3: Bond fissions featured in the proposed mechanistic hypothesis and the initial mechanism probe.
Scheme 4: Preparation of D-labelled alkynyl aziridine 4. DMP = Dess–Martin periodinane.
Scheme 5: Reaction of deuterated alkynyl aziridine 4 in the skeletal rearrangement reaction.
Scheme 6: Preparation of 13C-enriched alkynyl aziridines.
Scheme 7: Cycloisomerisation of 11 in the skeletal rearrangement reaction.
Scheme 8: Cycloisomerisation of 11 to give 2,5-disubstituted pyrrole.
Scheme 9: Cycloisomerisation of 14 in the skeletal rearrangement reaction.
Scheme 10: Cycloisomerisation of 15 in the skeletal rearrangement reaction.
Scheme 11: Revised mechanism for the formation of 2,4-isomers by skeletal rearrangement.
Scheme 12: Synthesis of alkynyl aziridines 30 and 31.
Scheme 13: Electronic effects on the outcome of the skeletal rearrangement processes.
Scheme 14: Mechanistic rationale for the deuterium labelling study using Ph3PAuCl/AgOTf.