Title
Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene
Grant Title
Natural Products Synthesis via Organoiron Methodology
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.
Recommended Citation
El-Mansy, Mohamed F.; Sar, Anobick; Lindeman, Sergey V.; and Donaldson, William A., "Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene" (2013). Natural Products Synthesis via Organoiron Methodology. 1.
https://epublications.marquette.edu/data_nps/1
Document Rights and Citation of Original
Chemistry, a European Journal, Vol. 19, No. 7 (February 2013): 2330-2336. DOI.