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Controllable Lewis Base-Catalyzed Three-Component Domino Reactions of Dioxazolones, Morita-Baylis-Hillman (MBH)
Jing Chen1, Haojie Gao1, Yong Chen1
1Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002, China.
Abstract:
Herein, we develop a novel Lewis base-catalyzed three-component divergent domino reaction of dioxazolones, Morita-Baylis-Hillman (MBH) carbonates, and alcohols/amines. On one hand, tertiary amine (triethylamine) operates as a dual nucleophilic catalyst to activate MBH carbonates and concurrently triggers the Lossen rearrangement, yielding functionalized carbamates. On the other hand, primary and secondary amines serve as substrates to generate low-reactivity ring-opened intermediates that can be efficiently intercepted by MBH carbonates to afford O-carbamoyl hydroxamates via an interrupted Lossen rearrangement. Overall, this protocol features transition-metal-free conditions and a broad substrate scope.
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