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Synthesis 2020; 52(23): 3632-3639
DOI: 10.1055/s-0040-1707352
DOI: 10.1055/s-0040-1707352
paper
DABCO-Catalyzed α-Regio- and Diastereoselective (3+2) Cycloadditions of Nitrone Ylides from Isatins and Activated Alkenes
We gratefully acknowledge the Natural Science Foundation of Zhejiang Province (Grant No. LY20B020012), the National Natural Science Foundation of China (Grant No. 21702185), Chongqing Research Program of Basic Research and Frontier Technology (Grant No. cstc2018jcyjAX0454), and the Science Foundation of Zhejiang Sci-Tech University (Grant No. 16062189-Y) for the financial support of this work.Further Information
Publication History
Received: 27 May 2020
Accepted after revision: 18 July 2020
Publication Date:
20 August 2020 (online)
Abstract
α-Regio- and diastereoselective (3+2) cycloadditions of nitrone ylides derived from isatins with activated alkenes have been demonstrated. This mild protocol allows rapid access to a wide range of 3′,5′-diaryl-1′-hydroxy-2-oxospiro[indoline-3,2′-pyrrolidine] derivatives by using DABCO as an efficient catalyst. This method could also be carried out through three-component reaction efficiently in good yields and excellent diastereoselectivity.
Key words
nitrone ylide - cyclization - spirooxindole - regioselectivity - diastereoselectivity - isatinSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707352.
- Supporting Information
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- 14 The structures of 3l and 3v were determined by single-crystal X-ray diffraction analyses. CCDC 1991838 for 3l and CCDC 2016378 for 3v contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures. For details see also the Supporting Information.
For recent selective reviews on cycloaddition reactions, see:
For recent selected reviews on 1,3-dipolar cycloaddition reaction, see:
For recent selected examples, see:
For selected reviews on azomethine ylides, see:
For selected reviews, see:
For selected examples, see: