双环化合物往往是天然产物和药物分子中的优势核心骨架，合成这些分子时常常面临的挑战是如何高效地构建目标分子中的环系骨架。考虑最终产物中要去除金属杂质的困难性，有机催化的合成双环化合物方法是一个有效的途径。有机膦催化的串联反应是一个构筑各种环状化合物的有效平台，但主要用在单环的合成，而有机膦催化的分子间反应直接用于双环体系的合成几乎是空白。针对这一问题，本项目拟在以前工作的基础上，采用有机膦催化的连续环化的策略，选取γ-取代丁二烯酸酯和MBH加成产物作为关键底物，通过调控催化剂，底物和催化模式的方法，发展有机膦催化的连续环化合成双环化合物的新方法；同时，利用手性膦催化剂研究其不对称反应，用计算化学的方法研究反应机理。预计本研究将为双环化合物[m, n, 0]（m=3，4; n=1, 2, 3,）的合成提供新方法，同时发现一些基于γ-取代丁二烯酸酯和MBH加成产物作为新合成子的反应。

Bicyclic skeletons represent privileged structural motifs in natural products and pharmaceuticals, it is a great challenge that the development of a more efficient strategy to construct bicyclic compounds. Since removal of residual metallic impurities from pharmaceutical products is difficult and increases the final cost, it is important to develop metal-free reactions, however, organocatalyzed reactions that enable the construction of bicyclic compounds remain rare. Thus, the development of an organocatalyzed strategy to construct bicyclic compounds should be an attractive and promising challenge. Nucleophilic phosphine catalysis has been established as a reliable platform for the efficient assembly of a wide array of single cyclic products from simple substrates, however, phosphine-catalyzed intermolecular annulation reactions to construct bicyclic compounds have been rarely reported. In order to solve this problems, based on our previous work, in this project a new strategy for the synthesis of bicyclic compounds will be developed through a phosphine-catalyzed sequential annulation reaction, the key substrates of γ-sbustituted allenoate and MBH adducts will be chosen, then, by adjusting the catalyst, and other reactive partner to realize the new sequential annulation reaction of γ-sbustituted allenoate or MBH adducts for the synthesis of bicyclic compounds[m, n, 0]（m=3，4; n=1, 2, 3,）, the asymmetric version of these reactions will be tested by the chiral phosphine catalyst, the reaction mechanism will be studied by DFT calculation.