Enantioselective Friedel–Crafts Alkylation of Furans with <i>o</i>-Quinone Methide Using a Chiral Oxazaborolidinium Ion Catalyst
Yoon Sung Cho, Seung Tae Kim, Do Hyun Ryu
Abstract
A chiral Lewis acid-catalyzed enantioselective Friedel–Crafts furan alkylation with in situ-generated o-quinone methides has been developed. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99%) with excellent enantioselectivity (up to >99% ee).
Topics & Concepts
Enantioselective synthesisFriedel–Crafts reactionChemistryAlkylationCatalysisFuranYield (engineering)Lewis acids and basesOrganic chemistryQuinoneMedicinal chemistryMaterials scienceMetallurgySynthesis of Indole DerivativesAxial and Atropisomeric Chirality SynthesisCarbohydrate Chemistry and Synthesis