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

Authors

Rajesh K. Pandey, Marquette University
Lizhu Wang
Nathaniel J Wallock, Marquette UniversityFollow
Sergey Lindeman, Marquette UniversityFollow
William Donaldson, Marquette UniversityFollow

Document Type

Article

Publication Date

2008

Publisher

American Chemical Society

Source Publication

Journal of Organic Chemistry

Source ISSN

0022-3263

Abstract

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.

Comments

Accepted version. Journal of Organic Chemistry, Volume 73, No. 18. (2008) pp 7236-7245. DOI. © 2008 American Chemical Society. Used with permission.

Recommended Citation

Pandey, Rajesh K.; Wang, Lizhu; Wallock, Nathaniel J; Lindeman, Sergey; and Donaldson, William, "Reactivity of (2-alkenyl-3-pentene-1,5-diyl)iron complexes: preparation of functionalized vinylcyclopropanes and cycloheptadienes" (2008). Chemistry Faculty Research and Publications. 48.
https://epublications.marquette.edu/chem_fac/48