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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| Authors: | Boqi Gu Shuxiao Wu Hui Xu Wulin Yang Zhixiang Liu Weiping Deng |
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| Affiliation: | 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 |
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| Abstract: | ![]()
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). |
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| Keywords: | Chiral secondary amine [3 + 3] Annulation Azomethine imines Asymmetric synthesis |
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