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Catalytic Enantioselective Allylic C–F Bond Functionalization

Minyan Wang, Zhaungzhi Shi

2020Chemistry Letters34 citationsDOIOpen Access PDF

Abstract

Abstract Catalytic enantioselective defluorinative functionalization of easily accessible allylic fluorines is well recognized as one of the most attractive strategies for creating allylic stereogenic centers with high enantioselectivity. This highlight review precisely aims to summarize the recent developments of this area mainly from the following six aspects: enantioselective defluoroarylation, enantioselective defluoroalkylation, enantioselective defluoroborylation, enantioselective defluorosilylation, enantioselective defluorohydrolation, and desymmetrization of difluoromethylene groups. Primarily, these reactions occur through two pathways, including β-fluorine elimination and C–F oxidative addition. Despite this, the mechanisms and limitations of these strategies have been a focus, and it is hoped that this review will provide a comprehensive overview to evaluate the prospects of this rapidly emerging field.

Topics & Concepts

Enantioselective synthesisAllylic rearrangementStereocenterDesymmetrizationChemistryCombinatorial chemistryCatalysisOrganic chemistryFluorine in Organic ChemistryAsymmetric Synthesis and CatalysisCyclopropane Reaction Mechanisms