金属卡宾是一类非常重要的两亲（亲电和亲核）有机合成子，广泛的应用于不对称催化反应中。杂原子亲核试剂与金属卡宾的不对称催化反应已有较多的报道，但碳原子亲核试剂参与的类似反应还不多见。富电子共轭二烯作为一类重要的碳亲核试剂，进攻金属卡宾引发的不对称[4+1]环加成反应在一步构建多取代手性环戊烯化合物上具有潜在的应用价值，但却未能获得有机化学家们的关注。本项目拟研究富电子共轭二烯或其衍生物与重氮化合物的不对称[4+1]环加成反应。对钌、铑、钯、铜、铱等金属和手性配体进行筛选，控制反应的选择性，构建高光学活性、高度官能化、具有全碳季碳结构的环戊烯衍生物。本方法学有望为多取代环戊烯衍生物的合成提供一条新的途径。

Metal carbene are versatile synthetic synthons in organic synthesis, it could act as electrophiles or nucleophiles in the asymmetric reactions. The asymmetric catalytic reactions of heteroatom nucleophiles with metal carbene have been widely studied. In contrast, carbon nucleophiles have received less attention so far. Electron-rich conjugated dienes are one type of most important nucleophiles, the tandem [4+1] cycloaddition reaction in which the metal carbene is attacked by carbon nucleophiles of electron-rich dienes may be proved to have obvious potential in the construction of multisubstituted cyclopentene derivatives. The proposal aims at the design of the asymmetric [4+1] cycloaddition reactions of diazo compounds with electron-rich conjugated diene and derivatives. Screening of metal catalysts such as ruthenium, rhodium, palladium, copper and iridium as well as the investigation of the chiral ligands are expected to realize the asymmetric version of the reaction, thereby providing a rapid, efficient access to structurally and optically enriched cyclopentene derivatives, which bearing one all-carbon quaternary stereocenter. The methodology is to be important with regard to synthetic applications in the synthesis of multisubstituted cyclopentene derivatives.