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First enantioselective synthesis of gingesulfonic acids and unequivocal determination of their absolute stereochemistry.

Grazia BencivenniMaria MocciaAndrea RavelliMalachi W Gillick-HealyBrian G KellyMauro F A Adamo
Published in: Organic & biomolecular chemistry (2020)
Herein we report the first organocatalysed enantioselective synthesis of gingesulfonic acids and shogasulfonic acids via a mild and convenient aminothiourea-catalysed conjugate addition of bisulfite to the olefin moiety of α,β-unsaturated carbonyls-a technology previously reported by us. A series of optically active naturally occurring sulfonic acids are prepared in their natural and unnatural configurations, and their absolute configurations are unequivocally confirmed by single crystal X-ray diffractometry.
Keyphrases
  • high resolution
  • magnetic resonance
  • solid phase extraction
  • dual energy
  • contrast enhanced