title: New C-C coupling reaction of cyclic nitronates with carbon nucleophiles. Umpolung of the conventional reactivity of nitronates.
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.
authors.affiliation: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.
authors.forename: Vladimir O
authors.initials: VO
authors.lastname: Smirnov
authors.forename: Sema L
authors.initials: SL
authors.lastname: Ioffe
authors.forename: Alexander A
authors.initials: AA
authors.lastname: Tishkov
authors.forename: Yulia A
authors.initials: YA
authors.lastname: Khomutova
authors.forename: Ivan D
authors.initials: ID
authors.lastname: Nesterov
authors.forename: Michael Yu
authors.initials: MY
authors.lastname: Antipin
authors.forename: William A
authors.initials: WA
authors.lastname: Smit
authors.forename: Vladimir A
authors.initials: VA
authors.lastname: Tartakovsky