有机小分子催化作为一门环境友好的有机合成方法学在不对称催化合成中引起极大关注，但存在催化活性不高、底物适用性较窄等缺点。手性胺基-硫脲是一类具有双功能特性的有机小分子催化剂，可同时介导亲核、亲电试剂，在多种不对称催化反应中表现较好的活性和手性控制，但通常会因分子间或分子内氢键而失活。为了解决此问题，本项目拟设计合成一类新型手性胺基-硫脲催化剂分子，分子中采用非常规1,3-二胺骨架，同时在胺基中引入手性高位阻基团。结合前期研究基础，利用前手性三氟甲基砌块1b的多反应位点特性，发展两类新型催化不对称Michael/Aldol和aza-Michael/Aminolysis串联关环反应，实现系列多样性含三氟甲基手性杂环化合物（5-9元）的构筑。充分使用核磁共振、质谱、计算化学等手段深入探讨不对称串联反应的反应机理及立体控制，为进一步设计新型手性催化剂和不对称催化反应提供理论依据和奠定实验基础。

At present, organocatalysts have drawn great interest as they tend to be less toxic and more environmentally friendly than traditional metal-based catalysts. Although much progress in organocatalysis has been made, the development of chiral organocatalysts that are as reactive and stereoselective as some of the best transition-metal catalysts remains a considerable challenge. Chiral amine-thiourea catalysts with bifunctional groups work cooperatively to stabilize the transition state and accelerate the rate of the reaction. However, catalyst aggregation resulting from intra- or inter-molecular hydrogen-bonding decreases the catalytic activity. To address this problem, herein a novel type of bifunctional chiral amine-thiourea catalysts possessing a 1,3-diamine backbone and multiple sterogenic centers is to be synthesized, and applied into the construction of various chiral trifluoromethylated heterocycles by using versatile prochiral trifluoromethylated building block 1b. Such a study aims to explore asymmetric Michael/Aldol and asymmetric aza-Michael/Aminolysis tandem reactions, respectively, to achieve several classes of important 5-9 membered trifluoromethylated heterocycles in high yields and ee’s. Reactions and processes monitored by NMR, Mass spectroscopy, X-ray, CD, and density functional theory (DFT) calculations will be carried out to elucidate the plausible mechanism. These studies will promote the development of new catalysts and catalytic asymmetric reactions.