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8421763 
Journal Article 
N-(ethoxycarbonyl)ferrocenecarboxamide: Synthesis and use as the pronucleophile in the Mitsunobu reaction 
Wrona-Piotrowicz, A; Zakrzewski, J; Jerzykiewicz, L 
2011 
Yes 
Journal of Organometallic Chemistry
ISSN: 0022-328X
EISSN: 1872-8561 
Elsevier B.V. 
696 
23 
3826-3830 
English 
The title compound has been synthesized in the reaction of ferrocene with ethoxycarbonyl isocyanate in methanesulfonic acid. It has been found that it undergoes N-alkylation with benzyl alcohols under classical Mitsunobu conditions (PPh3/DEAD). However, in the reaction with cholesterol and stigmasterol O-alkylation with inversion of configuration occurred (confirmed by hydrolysis of the product obtained from cholesterol to epicholesterol). The structure of the product obtained from p-nitrobenzyl alcohol was determined by X-ray diffraction. © 2011 Elsevier B.V. All rights reserved. 
Cholesterol; Epicholesterol; Ethoxycarbonyl isocyanate; Ferrocene; Mitsunobu reaction; Stigmasterol