Organocatalytic asymmetric [3+3] annulation of isatin N,N’-cyclic azomethine imines with enals:Efficient approach to functionalized spiro N-heterocyclic oxindoles  

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作  者:Boqi Gu Shuxiao Wu Hui Xu Wulin Yang Zhixiang Liu Weiping Deng 

机构地区:[1]College of Pharmaceutical Sciences,Zhejiang Chinese Medical University,Hangzhou 310053,China [2]Shanghai Key Laboratory of New Drug Design,School of Pharmacy.East China University of Science and Technology,Shanghai 200237,China

出  处:《Chinese Chemical Letters》2021年第2期672-675,共4页中国化学快报(英文版)

基  金:supported by the National Natural Science Foundation of China (No.21572053);Opening Project of Zhejiang Provincial Preponderant and Characteristic Subject of Key University (Traditional Chinese Pharmacology),Zhejiang Chinese Medical University (No.ZYAOX2018029)。

摘  要:An unprecedented chiral secondary amine-catalyzed [3+3] annulation of isatin N,N’-cyclic azomethine imines with α,β-unsaturated aldehydes was developed.This strategy allowed the construction of structurally novel spiro N-heterocyclic oxindole derivatives in good yields(up to 91%) and good to excellent enantioselectivities(up to>99% ee),albeit with modest diastereoselectivities(up to 3.1:1 dr).

关 键 词:Chiral secondary amine [3+3]Annulation Azomethine imines Spiro N-heterocyclic oxindole Asymmetric synthesis 

分 类 号:O626.13[理学—有机化学]

 

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