Citation: Boqi Gu, Shuxiao Wu, Hui Xu, Wulin Yang, Zhixiang Liu, Weiping Deng. Organocatalytic asymmetric [3 + 3] annulation of isatin N,N'-cyclic azomethine imines with enals: Efficient approach to functionalized spiro N-heterocyclic oxindoles[J]. Chinese Chemical Letters, ;2021, 32(2): 672-675. doi: 10.1016/j.cclet.2020.06.010 shu

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

Boqi Gu ^b ,
Shuxiao Wu ^b ,
Hui Xu ^b ,
Wulin Yang ^b ,
Zhixiang Liu ^{a, *,} ,
Weiping Deng ^{a, b, *,}

a.
College of Pharmaceutical Sciences, Zhejiang Chinese Medical University, Hangzhou 310053, China
b.
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

zhixiangliu88@163.com

weiping_deng@ecust.edu.cn

Received Date: 16 May 2020
Revised Date: 5 June 2020
Accepted Date: 8 June 2020
Available Online: 9 June 2020

Figures(7)

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).
- Chiral secondary amine,
- [3 + 3] Annulation,
- Azomethine imines,
- Spiro N-heterocyclic oxindole,
- Asymmetric synthesis
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