New C−C Coupling Reaction of Cyclic Nitronates with Carbon Nucleophiles. Umpolung of the Conventional Reactivity of Nitronates

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posted on 2004-11-26, 00:00 authored by Vladimir O. Smirnov, Sema L. Ioffe, Alexander A. Tishkov, Yulia A. Khomutova, Ivan D. Nesterov, Michael Yu. Antipin, William A. Smit, Vladimir A. Tartakovsky

Cyclic six-membered nitronates 1 are involved in diastereoselective C−C coupling reactions with various nucleophiles in the presence of either catalytic or stoichiometric amounts of TBDMSOTf to give the previously unknown N-siloxytetrahydrooxazines. The intermediacy of N,N-bis(oxy)iminium cations was proven by NMR data.

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presence diastereoselective Carbon Nucleophiles cation siloxytetrahydrooxazine stoichiometric amounts New Cyclic Nitronates intermediacy NMR data Conventional Reactivity bi TBDMSOTf nucleophile Umpolung nitronate

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New C−C Coupling Reaction of Cyclic Nitronates with Carbon Nucleophiles. Umpolung of the Conventional Reactivity of Nitronates

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