Reactivity of (2-alkenyl-3-pentene-1,5-diyl)iron complexes: preparation of functionalized vinylcyclopropanes and cycloheptadienes.
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.
Pandey
Rajesh K
RK
Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, Wisconsin 53201-1881, USA.
Wang
Lizhu
L
Wallock
Nathaniel J
NJ
Lindeman
Sergey
S
Donaldson
William A
WA
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
D000475:Alkenes; D003508:Cycloheptanes; D003521:Cyclopropanes; D005290:Ferric Compounds; D008024:Ligands; D014753:Vinyl Compounds