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