Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene
Chemistry, a European Journal
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.
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.
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.