Organocatalytic Stereoselective[8+2]Cycloaddition of Tropones with Azlactones  

作　　者：Jinzhao Li Yuhao Mo Liqiao Yan Xiaoming Feng Zhishan Su Xiaohua Liu 

机构地区：[1]Key Laboratory of Green Chemistry and Technology,Ministry of Education,College of Chemistry,Sichuan University,Chengdu 610064

出　　处：《CCS Chemistry》2022年第2期650-659,共10页中国化学会会刊（英文）

摘　　要：Herein,we report an organocatalytic asymmetric[8+2]higher-order cycloaddition of tropones with azlactones employing bifunctional guanidines as hydrogen-bond-mediated catalysts via a 1,8-addition/annulation process.The reaction has a broad scope with respect to both cycloaddition partners and hence offers rapid access to an array of[5.3.0]bicyclic compounds with excellent outcomes[up to 95%yield,>19:1 diastereomeric ratio(dr),and 96%enantiomeric excess(ee)].Besides,the synthetic utility of the protocol provides rapid transformation into enantioenrichedα-amino acid derivatives.Moreover,the isolated[1,5]-H shift isomer,X-ray crystal structure of chiral guanidinium salt,and density functional theory(DFT)calculations provide convincing evidence for the interpretation of diastereo-and enantioselection.

关 键 词：asymmetric catalysis chiral guanidine higher-order cycloaddition TROPONE AZLACTONE α-amino acid DFT calculations 

分 类 号：O62[理学—有机化学]