手性含氮杂环骨架广泛存在于具有生理活性的天然产物以及手性药物分子中，同时也是非常重要的有机合成中间体。因此从合成化学的角度，发展高效构筑结构多样性的手性氮杂环骨架对新药发现和药物工艺创新都有重要的研究意义与潜在的应用前景。氮杂二烯作为一类简便易得的合成子，被广泛应用于氮杂环化合物的合成中；但是鲜见其应用于催化不对称合成的研究报道。本项目旨在研究利用氮杂二烯作为杂双烯反应组份，通过设计合适的亲双烯体或同时具有亲核与亲电反应位点的组份反应，结合新型手性催化体系或手性配体的开发，探索手性氮杂环骨架的高效立体选择性构建，丰富手性氮杂环合成方法学；进而将发展的高效催化体系应用于一些具有重要生理活性的关键手性中间体的合成。同时结合反应机理的研究，探索总结手性催化剂中的各种因素对催化活性和反应立体选择性的影响，揭示其不对称催化反应中的手性诱导、手性传递和手性放大的规律性。

Nitrogen-containing heterocycles are frequently found in many bioactive natural products, and they are also the core structures of active pharmaceutical ingredients and also synthetically useful building blocks. In terms of synthetic chemistry, developing efficient methodologies for the construction of diversified and enantiomerically enriched heterocycles is very important to new drug discovery and the innovation of key drug synthesis. Although readily-available azoalkenes have been commonly employed as key intermediates for the synthesis of various achiral nitrogen-containing heterocycles, they have seldom been employed as the synthons in catalytic asymmetric synthesis. This project will provide efficient and practical protocols for the asymmetric construction of enantioenriched nitrogen-containing heterocycles with high functionality via azoalkene-involved catalytic asymmetric cycloaddition reactions, in which various dienophiles or potential reactant partners containing both nucleophilic and electrophilic sites will be designed and tackled. To realize those objective, new chiral ligands or some novel catalytic system will be developed and evaluated with the application of some strategies, which should diversify the synthetic methodology of heterocycles. The asymmetric synthesis of some chiral drug or its key intermediates will be attempted with thus developed cycloaddition reactions. Meanwhile, mechanism study will be performed to investigate and summarize the steric effect, electronic effect of the chiral catalysts on the reactivities and stereoselectivities, and further to reveal the inherent regularity of chiral induction, transfer and amplification in asymmetric catalysis.