Yb(OTf)_(3)-Catalyzed Asymmetric[3+3]Cycloaddition of N-Vinyl Nitrones with Activated Cyclopropanes to Prepare 1,2-Oxazines  

作　　者：Yu-Zheng Wu Yue Leng Yi-Xin Chen Shi-Qiu Huang Ning Zou Chun-Hua Chen Dong-Liang Mo 

机构地区：[1]State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources,Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources(Ministry of Education of China),Collaborative Innovation Center for Guangxi Ethnic Medicine,School of Chemistry and Pharmaceutical Sciences,Guangxi Normal University,15 Yu Cai Road,Guilin,Guangxi 541004,China [2]Key Laboratory of Chemistry and Engineering of Forest Products,State Ethnic Affairs Commission,Guangxi Key Laboratory of Chemistry and Engineering of Forest Products,Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products,Schoolof Chemistry and ChemicalEngineering,Guangxi Minzu University,Nanning,Guangxi 530006,China [3]College of Chemistry and Chemical Engineering,Neijiang Normal University,Nejiang,Sichuan 641100,China

出　　处：《Chinese Journal of Chemistry》2025年第4期417-422,共6页中国化学(英文版)

基　　金：Financial support from the NSFC(22071035);Natural Science Foundation of Guangxi(2023GXNSFDA026025);Guangxi Science and Technology Plan Project(AD23026046);Graduate Innovation Training Program of Guangxi(YCSW2024160);Natural Science Foundation of Sichuan(2023NSFSC1087);Guangxi Bagui Young Scholar is greatly appreciated.

摘　　要：We described a Yb(OTf)_(3) combined with Pybox ligand catalyzed asymmetric[3+3]cycloaddition of N-vinyl cinnamaldehyde nitrones with activated cyclopropanes to prepare various functionalized 1,2-oxazines in 24%—95% yields and 22%—96%ee.Experimental results revealed that the reaction underwent a domino[3+3]cycloaddition,dealkenylation,and aza-1,4-addition in three steps.The chiral 1,2-oxazine could be obtained in gram scales and easily converted into various 1,2-oxazine scaffolds.The present method features broad substrate scope,good functional group compatibility,three-component domino reaction,and asymmetric[3+3]cycloaddition of N-vinyl nitrones with activated cyclopropanes.

关 键 词：CYCLOADDITION Cyclopropane NITRONE 1 2-Oxazine Asymmetric catalysis Domino reactions Michael addition N-Heterocycle 

分 类 号：O62[理学—有机化学]