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

Autor:	Grazia Bencivenni, Andrea Ravelli, Brian G. Kelly, Malachi W. Gillick-Healy, Maria Moccia, Mauro F. A. Adamo
Rok vydání:	2020
Předmět:	Bisulfite Olefin fiber Stereochemistry Chemistry Organic Chemistry Enantioselective synthesis Moiety Physical and Theoretical Chemistry Optically active Biochemistry Single crystal Conjugate
Zdroj:	Organic & Biomolecular Chemistry. 18:1091-1094
ISSN:	1477-0539 1477-0520
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::edeb5f0eabba2dce79b91aaa193b5fb6 https://doi.org/10.1039/c9ob02662b Zobrazit plný text záznamu