Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene

Authors

Mohamed F. El-Mansy, Marquette University
Anobick Sar, Marquette University
Sergey Lindeman, Marquette UniversityFollow
William Donaldson, Marquette UniversityFollow

Document Type

Article

Publication Date

2-2013

Source Publication

Chemistry, a European Journal

Source ISSN

0947-6539

Abstract

The racemic (6-cyclo-heptadienyl)Fe(CO)₃⁺ cation ((±)-7), prepared from cyclooctatetraene, was treated with a variety of carbon and heteroatom nucleophiles. Attack took place at the less hindered C¹ dienyl carbon and decomplexation of the (cycloheptadiene)Fe(CO)₃ complexes gave products rich in functionality for further synthetic manipulation. In particular, a seven-step route was developed from racemic (6-styryl-2,4-cycloheptadien-1-yl)phthalimide ((±)-9 d) to afford the optically active aminocycloheptitols (−)-20 and (+)-20.

Comments

Accepted version. Chemistry, a European Journal, Vol. 19, No. 7 (February 2013): 2330-2336. DOI. © 2013 Wiley-VCH Verlag 2013. Used with permission

The spectral data used in the research for this article may be found here.

Recommended Citation

El-Mansy, Mohamed F.; Sar, Anobick; Lindeman, Sergey; and Donaldson, William, "Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene" (2013). Chemistry Faculty Research and Publications. 266.
https://epublications.marquette.edu/chem_fac/266