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硝酮的合成与[3+2]环加成反应研究进展
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Abstract:
硝酮是一类重要的1,3-偶极化合物，是构建异噁唑烷、异噁唑啉等五元氮氧杂环的关键合成砌块。本文系统综述硝酮的代表性合成方法，重点阐述其[3+2]环加成反应在有机催化、协同催化、无催化、电催化四大体系的研究进展，总结各催化体系的反应机理、收率、立体选择性及底物适用性；同时介绍硝酮在天然产物全合成、手性合成砌块与生物医学领域的应用，展望硝酮化学向温和、绿色、无金属、高选择性方向发展的趋势，为含氮杂环的高效精准合成提供参考。
Nitrones are important 1,3-dipolar compounds and key synthetic building blocks for constructing five-membered nitrogen-oxygen heterocycles such as isoxazolidines and isoxazolines. This paper systematically reviews the representative synthetic methods of nitrones, and emphatically summarizes the research progress of their [3+2] cycloaddition reactions in four catalytic systems: organocatalysis, cooperative catalysis, catalyst-free system and electrocatalysis. The reaction mechanism, yield, stereoselectivity and substrate applicability of each catalytic system are discussed. In addition, the applications of nitrones in the total synthesis of natural products, chiral synthetic building blocks and biomedicine are introduced. The development trend of nitrone chemistry toward mild, green, metal-free and highly selective synthesis is prospected, which provides a reference for the efficient and precise synthesis of nitrogen-containing heterocycles.
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