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Issue 13, 2018
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Organocatalytic asymmetric [3 + 2] annulation of 1,4-dithiane-2,5-diol with azlactones: access to chiral dihydrothiophen-2(3H)-one derivatives

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Abstract

Herein, the first organocatalyst-mediated enantioselective [3 + 2] annulations of 1,4-dithiane-2,5-diol with various azlactones utilizing C4 and C5 reactivity using squaramide as the catalyst in a ring-opening manner have been reported. This protocol provides convenient access to enantioenriched substituted dihydrothiophen-2(3H)-one derivatives. Excellent isolated yields and moderate to good enantioselectivities have been achieved.

Graphical abstract: Organocatalytic asymmetric [3 + 2] annulation of 1,4-dithiane-2,5-diol with azlactones: access to chiral dihydrothiophen-2(3H)-one derivatives

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Publication details

The article was received on 20 Mar 2018, accepted on 07 May 2018 and first published on 09 May 2018


Article type: Research Article
DOI: 10.1039/C8QO00305J
Citation: Org. Chem. Front., 2018,5, 2040-2044
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    Organocatalytic asymmetric [3 + 2] annulation of 1,4-dithiane-2,5-diol with azlactones: access to chiral dihydrothiophen-2(3H)-one derivatives

    J. Yu, L. Yu, X. Zhao, L. Gan, W. Zhu, Z. Wang, R. Wang and X. Jiang, Org. Chem. Front., 2018, 5, 2040
    DOI: 10.1039/C8QO00305J

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