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

doi:10.1039/c8ob00768c

Paper

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

Published May 30, 2018 · O. Bakulina, D. Dar'in, M. Krasavin

Organic & biomolecular chemistry

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6

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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.

Study Snapshot

A mixed carboxylic-sulfonic anhydride can efficiently produce water-soluble -lactams via a Staudinger-type reaction, with some preference for trans-isomer formation and some pure diastereomers.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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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References

Citations

Recent advances in β-lactam synthesis.

Recent advances in photo- and transition metal-catalysis have led to new methods for -lactam synthesis, including ligand assisted metal catalyzed C-H activation/intermolecular oxidative amidation.

Four-membered ring systems

Four-membered heteroatom-containing cycles show promising synthesis and reactivity, with new developments in -lactam chemistry.

Advances in synthesis and chemistry of aziridines

Advances in aziridine synthesis and chemistry have significantly improved the ability to synthesize enantiopure forms and their reactivity as building blocks in organic synthesis.