The first trapping of N-acyliminium ions by in situ generated carbaminic acid (product of carbon dioxide (CO2) and amine) is reported. This catalyst-free reaction provides a convenient and feasible approach to prepare N-acyl thia- and oxazolidinyl carbamates with good functional-group compatibility and high efficiency under green conditions. Furthermore, the multicomponent method features a broad substrate scope, facile product diversification, smooth scale-up and notable potential for polymer applications.
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-Acyliminium ions generated from enamidyl vinyl ketones provided cyclopentenoid-fused diazepines diastereoselectively using BF·EtO in one pot through a domino -acyliminium ion trapping/Nazarov reaction, simultaneously generating three new stereogenic centers. The particular structural design of the cross-conjugated dienone dictates the torquoselectivity observed in this polarized Nazarov reaction. Various -bridgehead polycyclic scaffolds of putative pharmacological interest were obtained.
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Institut für Chemie, Carl von Ossietzky Universität Oldenburg, P. O. Box 2503, Carl-von-Ossietzky-Str. 9-11, 26111 Oldenburg, Germany.
The first trapping of N-acyliminium ions by in situ generated carbaminic acid (product of carbon dioxide (CO2) and amine) is reported. This catalyst-free reaction provides a convenient and feasible approach to prepare N-acyl thia- and oxazolidinyl carbamates with good functional-group compatibility and high efficiency under green conditions. Furthermore, the multicomponent method features a broad substrate scope, facile product diversification, smooth scale-up and notable potential for polymer applications.
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