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Issue 7, 2018
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Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with N-sulfonylimines: a facile synthesis of tetrahydropyridines

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Abstract

Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with N-sulfonylimines for the synthesis of 1,2,3,6-tetrahydropyridines is developed. The reaction proceeds smoothly under mild reaction conditions to give the annulation products in moderate to excellent yields. Mechanistic exploration of this new annulation shows that the δ-sulfonamido-substituted enone and the N-sulfonylimine serve as C5 and C1 synthons to furnish the annulation, respectively. Using chiral phosphine as the catalyst, an asymmetric variant of the model reaction gave the chiral product in up to 73% ee.

Graphical abstract: Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with N-sulfonylimines: a facile synthesis of tetrahydropyridines

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Publication details

The article was received on 18 Oct 2017, accepted on 02 Jan 2018 and first published on 05 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC04515H
Citation: Chem. Sci., 2018,9, 1831-1835
  • Open access: Creative Commons BY license
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    Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with N-sulfonylimines: a facile synthesis of tetrahydropyridines

    L. Zhou, C. Yuan, Y. Zeng, H. Liu, C. Wang, X. Gao, Q. Wang, C. Zhang and H. Guo, Chem. Sci., 2018, 9, 1831
    DOI: 10.1039/C7SC04515H

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