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Issue 13, 2018
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Enantioselective [3 + 2] cycloaddition and rearrangement of thiazolium salts to synthesize thiazole and 1,4-thiazine derivatives

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Abstract

Highly efficient asymmetric [3 + 2] cycloaddition reactions of thiazolium salts with a variety of electron-deficient 2-π components were achieved by chiral N,N′-dioxide/metal complex catalysts, providing a convenient route to access enantioenriched hydropyrrolo-thiazoles. The oxathiazine and sulfinate could be readily obtained by the oxidation of the hydropyrrolo-thiazole. Moreover, through ingenious collaboration of chiral catalysts with basic additives, the first cascade cycloaddition/rearrangement reaction with β,γ-unsaturated α-ketoesters was realized, and various pyrrolo-[1,4]thiazine derivatives were afforded in excellent results.

Graphical abstract: Enantioselective [3 + 2] cycloaddition and rearrangement of thiazolium salts to synthesize thiazole and 1,4-thiazine derivatives

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Publication details

The article was received on 10 Apr 2018, accepted on 26 May 2018 and first published on 28 May 2018


Article type: Research Article
DOI: 10.1039/C8QO00370J
Citation: Org. Chem. Front., 2018,5, 2126-2131
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    Enantioselective [3 + 2] cycloaddition and rearrangement of thiazolium salts to synthesize thiazole and 1,4-thiazine derivatives

    X. Zhang, X. Liu, J. Zhang, D. Zhang, L. Lin and X. Feng, Org. Chem. Front., 2018, 5, 2126
    DOI: 10.1039/C8QO00370J

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