An Enantioselective Approach to Heteroatom-Containing Bicyclic Derivatives via Inverse-Electron-Demand Diels-Alder Reactions  

作　　者：Jun-Xiong He Xu-Ge Si Qi-Tao Lu Qian-Wei Zhang Quan Cai 

机构地区：[1]Department of Chemistry,Research Center for Molecular Recognition and Synthesis,220 Handan Road,Fudan University,Shanghai 200433,China

出　　处：《Chinese Journal of Chemistry》2023年第1期21-26,共6页中国化学（英文版）

基　　金：the National Natural Science Foundation of China(Grant No.22071030);Fudan University for financial support。

摘　　要：Chiral heteroatom-containing bicyclic scaffolds are important pharmacophores and prevalent in bioactive natural products and drug molecules.Herein,we report a unified approach for the divergent synthesis of chiral heteroatom-containing bicyclic derivatives by lanthanide(lil)-catalyzed asymmetric inverse-electron-demand Diels-Alder reactions of 2-pyrones.These reactions occur with vari-ous readily available dihydropyrroles and dihydrofurans as dienophiles,providing a step-economical synthetic platform for densely functionalized ciss-hydroindoles and cis-hydrobenzofurans with excellent yields and enantioselectivities.The synthetic utility of this approach is demonstrated by the concise synthesis of(-)-α-lycorane and(-)-lycorine alkaloids.

关 键 词：Asymmetric catalysis HETEROCYCLES Total synthesis 2-Pyrones Inverse-electron-demand Diels-Alder reaction Cycloaddition 

分 类 号：O62[理学—有机化学]