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Issue 21, 2018
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Mixed carboxylic–sulfonic anhydride in reaction with imines: a straightforward route to water-soluble β-lactams via a Staudinger-type reaction

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Abstract

The first example of employing a mixed carboxylic–sulfonic anhydride in reaction with imines is reported. Unlike its well-studied isostere homophthalic anhydride, benzo[c][1,2]oxathiin-3(4H)-one 1,1-dioxide gave no product of a formal [4 + 2] cycloaddition and only followed an alternative reaction pathway toward β-lactams, presumably, via a formal [2 + 2] cycloaddition (a Staudinger-type reaction). Optimized reaction conditions involve the use of triethylamine as a base promoter, which also allows isolating the product β-lactam benzene sulfonic acids as respective triethylammonium salts by conventional column chromatography. The reaction shows some preference to trans-isomer formation; pure diastereomers can be isolated in some cases.

Graphical abstract: Mixed carboxylic–sulfonic anhydride in reaction with imines: a straightforward route to water-soluble β-lactams via a Staudinger-type reaction

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Publication details

The article was received on 01 Apr 2018, accepted on 08 May 2018 and first published on 08 May 2018


Article type: Paper
DOI: 10.1039/C8OB00768C
Citation: Org. Biomol. Chem., 2018,16, 3989-3998
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    Mixed carboxylic–sulfonic anhydride in reaction with imines: a straightforward route to water-soluble β-lactams via a Staudinger-type reaction

    O. Bakulina, D. Dar'in and M. Krasavin, Org. Biomol. Chem., 2018, 16, 3989
    DOI: 10.1039/C8OB00768C

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