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Issue 47, 2018
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Construction of spirothioureas having an amino quaternary stereogenic center via a [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates

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Abstract

A useful and convenient strategy for the diastereoselective synthesis of spirothioureas having an amino quaternary stereogenic center via a [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates was established. A diverse set of spirooxindole derivatives were synthesized in good to excellent yields and diastereoselectivities. Good enantioselectivities (up to 96 : 4 er) were obtained in the subsequent asymmetric study.

Graphical abstract: Construction of spirothioureas having an amino quaternary stereogenic center via a [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates

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Publication details

The article was received on 06 Nov 2018, accepted on 19 Nov 2018 and first published on 19 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02748J
Citation: Org. Biomol. Chem., 2018,16, 9218-9222
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    Construction of spirothioureas having an amino quaternary stereogenic center via a [3 + 2] annulation of 3-isothiocyanato oxindoles with 2-aminoacrylates

    H. Gui, Y. Wei and M. Shi, Org. Biomol. Chem., 2018, 16, 9218
    DOI: 10.1039/C8OB02748J

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