Chiral Bronsted acid-catalyzed intramolecular S_N2' reaction for enantioselective construction of a quaternary stereogenic center.

ABSTRACT: An enantioselective intramolecular anti-S_N2' cyclization reaction for the construction of a quaternary stereogenic center was accomplished through the activation of the leaving group using a binaphthol-derived phosphoramide as the chiral Brønsted acid catalyst. The present allylic substitution reaction is beneficial not only for the regioselective nucleophilic substitution at the multi-substituted site of the double bond but also for controlling the stereochemical outcome because of using a geometrically defined double bond. Indeed, the reaction afforded synthetically useful amino alcohol derivatives having a tetra-substituted carbon center in a highly enantioselective manner in most cases, in which the modification of the sulfonamide unit of the phosphoramide catalyst wa

SUBMITTER: Shimizu M 

PROVIDER: S-EPMC6050593 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature