Reactivity of (2-alkenyl-3-pentene-1,5-diyl)iron complexes: preparation of functionalized vinylcyclopropanes and cycloheptadienes

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Journal of Organic Chemistry


The reactivity of (2-alkenyl-3-pentene-1,5-diyl)iron complexes toward olefin metathesis, cycloaddition, and mild oxidations (MnO2 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.


Journal of Organic Chemistry, Volume 73, No. 18. (2008) pp 7236-7245. DOI: 10.1021/jo801446q

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