New route to functionalized cyclohexenes from nitromethane and electrophilic alkenes without solvent under focused microwave irradiation

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David Michaud, Sahar Abdallah-El Ayoubi, Marie-Joëlle Dozias, Loïc Toupet, Françoise Texier-Boullet and Jack Hamelin


Abstract

Nitromethane reacts via a diastereoselective double Michael addition with electrophilic alkenes activated by cyano and methoxycarbonyl groups [XC6H4CH[double bond, length as m-dash]C(CN)CO2Me] in the presence of catalytic amounts of piperidine under solvent-free conditions coupled with focused microwave irradiation to afford new, highly functionalized cyclohexenes; no cyclopropane formation is observed.


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