Kinetic resolution of racemic tertiary allylic alcohols through S<sub>N</sub>2′ reaction using a chiral bisphosphoric acid/silver(<scp>i</scp>) salt co-catalyst system
Satavisha Kayal, Jun Kikuchi, Naoya Shinagawa, Shigenobu Umemiya, Masahiro Terada
Abstract
A highly efficient KR of racemic tertiary allylic alcohols was developed through the intramolecular S N 2′ reaction using the chiral bisphosphoric acid/silver carbonate co-catalyst system, affording cis -epoxides and recovered alcohols in a high s -factor.
Topics & Concepts
Allylic rearrangementKinetic resolutionChemistryCatalysisEnantioselective synthesisIntramolecular forceSalt (chemistry)DieneOrganic chemistryEnantiomerCombinatorial chemistrySubstitution reactionNatural rubberAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods