New C−C Coupling Reaction of Cyclic Nitronates with Carbon Nucleophiles. Umpolung of the Conventional Reactivity of Nitronates
The Journal of Organic Chemistry2004Vol. 69(24), pp. 8485–8488
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Vladimir O. Smirnov, Sema L. Ioffe, Alexander A. Tishkov, Yulia A. Khomutova, И. Д. Нестеров, M. Yu. Antipin, William A. Smit, Vladimir A. Tartakovsky
Abstract
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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