Ac-L-Methionine-Catalyzed, Nitrite-Triggered Cycloaddition Reaction Between Bromide and Alkyne/Alkene: A step-economical reaction for modular synthesis

The development of modular, chemically diverse and regioselective reactions for expanding the cycloaddition reaction toolbox hinges heavily on a strict functional 1,3-dipole and dipolarophile pairing exploration. In this study, we disclosed a step-economic, nitrite-triggered cycloaddition reaction between bromide and alkyne/alkene for modular assembly of isoxazoles (or isoxazolines). This process underwent an in-situ Ac-L-methionine (S11)-catalyzed sulfur ylide generation, nitrite-triggered the generation of a sulfonium masked 1,3-dipole, as well as subsequent cascade cycloaddition with alkyne (or alkene) by the simultaneous releasing of Ac-L-methionine (S11). With intrinsic advantages of high regio-selectivity, excellent efficiency, wide functionality tolerance, biocompatible condition and operational simplicity, this reaction is robust for the direct diversification of pharmaceutics and bio-relevant motifs. Moreover, this intermolecular cycloaddition reaction could be well expanded to the intramolecular cycloaddition for fused-ring isoxazoles and proximity sulfide induced cycloaddition for the specific methionine modification.

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