title: Enone-alkyne reductive coupling: a versatile entry to substituted pyrroles.
abstract: The reductive coupling of enones or enals with alkynes, followed by olefin oxidative cleavage and Paal-Knorr cyclization, provides a versatile entry to a variety of pyrrole frameworks. A number of limitations of alternate entries to the requisite 1,4-dicarbonyl intermediate are avoided. Classes of pyrroles that are accessible by this approach include 2,3-, 2,4-, 1,2,3-, 1,2,4-, 2,3,5-, and 1,2,3,5-substituted monocyclic pyrroles as well as a number of fused-ring polycyclic derivatives.
authors.affiliation: Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.
authors.forename: Benjamin B
authors.initials: BB
authors.lastname: Thompson
authors.forename: John
authors.initials: J
authors.lastname: Montgomery
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D000480:Alkynes; D006571:Heterocyclic Compounds; D007659:Ketones; D011758:Pyrroles