title: Reactivity of (2-alkenyl-3-pentene-1,5-diyl)iron complexes: preparation of functionalized vinylcyclopropanes and cycloheptadienes.
abstract: The reactivity of (2-alkenyl-3-pentene-1,5-diyl)iron complexes toward olefin metathesis, cycloaddition, and mild oxidations (MnO 2 or mCPBA) was examined. Cycloaddition reactions were observed to occur with modest diastereoselectivity (33-63% de). Decomplexation of the (3-pentenediyl) ligand may be accomplished by oxidation with either CAN or alkaline hydrogen peroxide to afford vinylcyclopropanecarboxylates or divinylcyclopropanecarboxylates. Reduction of the latter, followed by Cope rearrangement generates cycloheptadienylmethanols. These studies demonstrate that (2-alkenyl-3-pentene-1,5-diyl)iron complexes can serve as organometallic scaffolds for the preparation of a wide variety of structural motifs containing up to 5 contiguous stereocenters.
authors: Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, Wisconsin 53201-1881, USA.
authors: Rajesh K
authors: RK
authors: Pandey
authors: Lizhu
authors: L
authors: Wang
authors: Nathaniel J
authors: NJ
authors: Wallock
authors: Sergey
authors: S
authors: Lindeman
authors: William A
authors: WA
authors: Donaldson
mesh_terms: D000475:Alkenes / Q000737:chemistry; D003500:Cyclization; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D005290:Ferric Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D003508:Cycloheptanes; D003521:Cyclopropanes; D005290:Ferric Compounds; D008024:Ligands; D014753:Vinyl Compounds