氮杂亚甲基醌及其衍生物是一类高活性、不稳定的反应中间体。由于其结构的特殊性，存在着电荷分离的极限共振式，在热力学的驱动力下利于恢复芳香性，因此氮杂亚甲基醌中间体很难在正常条件下存在。该中间体的结构仍然处于假想阶段，目前还没有具体的光谱检测到氮杂亚基醌的存在。同时，基于氮杂亚甲基醌的手性催化反应也只有零星的报道。本项目希望发展原位产生氮杂亚甲基醌中间体的合成方法，利用原位的光谱技术定性和定量表征氮杂亚甲基醌中间体，在此基础上，发展基于氮杂亚甲基醌中间体的手性催化反应。包括亲核加成反应、手性环化反应、分子内脱羧加成反应和手性氢化反应，建立起相应的方法学。通过这些研究，开发具有自主知识产权的不对称转化技术，促进我国有机合成反应的研究与发展，推动在相关化学工业中的应用。

N-Quinone methides (N-QMs) are important intermediates in organic synthesis and materials chemistry as well as biological processes. N-QMs are much more polarized and thus more reactive than QMs. Moreover, the strongly thermodynamic drive to undergo rearomatization also accounts for their high reactivity. Therefore, N-QMs are not stable enough to be isolated and characterization under normal circumstances. In this project, we will focus on exploring the asymmetric transformations of N-quinone methides derived from anilines. Transformations include asymmetric hydrogenation, addition, and cyclizations. The above methododlogy will be applied to synthesis of some natural occuring products and chiral drugs. By doing so, we will try to invent new asymmetric transformation technologies and push forward the applications in the corresponding industries.