title: Carbon-carbon bond formation and pyrrole synthesis via the [3,3] sigmatropic rearrangement of O-vinyl oxime ethers.
abstract: A new method for the synthesis of 2,4- and 2,3,4-substituted pyrroles in two or three steps from commercially available ketones and allyl hydroxylamine is described. An iridium-catalyzed isomerization reaction has been developed to convert O-allyl oximes to O-vinyl oximes, which undergo a facile [3,3] rearrangement to form 1,4-imino aldehyde Paal-Knorr intermediates that cyclize to afford the corresponding pyrroles. Optimization and examples of the isomerization and pyrrole formation are discussed.
authors.affiliation: Department of Chemistry, University of Illinois, Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
authors.forename: Heng-Yen
authors.initials: HY
authors.lastname: Wang
authors.forename: Daniel S
authors.initials: DS
authors.lastname: Mueller
authors.forename: Rachna M
authors.initials: RM
authors.lastname: Sachwani
authors.forename: Hannah N
authors.initials: HN
authors.lastname: Londino
authors.forename: Laura L
authors.initials: LL
authors.lastname: Anderson
mesh_terms: D002244:Carbon / Q000737:chemistry*; D003500:Cyclization; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004987:Ethers; D010091:Oximes; D011758:Pyrroles; D002244:Carbon