N-(ethoxycarbonyl)ferrocenecarboxamide: Synthesis and use as the pronucleophile in the Mitsunobu reaction

作者：Wrona Piotrowicz Anna; Zakrzewski Janusz^*; Jerzykiewicz Lucjan

来源：Journal of Organometallic Chemistry, 2011, 696(23): 3826-3830.

DOI：10.1016/j.jorganchem.2011.08.030

• Ferrocene
• Ethoxycarbonyl isocyanate
• Mitsunobu reaction
• Cholesterol
• Epicholesterol
• Stigmasterol

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.

• 出版日期2011-11-15