First enantioselective synthesis of gingesulfonic acids and unequivocal determination of their absolute stereochemistry. Issue 6 (29th January 2020)

• Record Type: Journal Article
• Authors: Bencivenni, Grazia; Moccia, Maria; Ravelli, Andrea; Gillick-Healy, Malachi W.; Kelly, Brian G.; Adamo, Mauro F. A.
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 6(2020)
• Page Start: 1091
• Page End: 1094
• Publication Date: 2020-01-29
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob02662b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The first enantioselective synthesis of gingesulfonic acids and shogasulfonic acids is herein reported alongside their absolute configurations, unequivocally confirmed by single crystal X-ray diffractometry. Abstract : 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.