Recent Advances in Catalytic Enantioselective Fluorination of Active Methines

Abstract

Organofluorine compounds are central importance in the pharmaceutical and agrochemical industries because the replacement of a hydrogen with a fluorine atom in biologically active molecules can be beneficial in terms of physicochemical properties and biological activities. Thus, the development of effective methodologies for the preparation of chiral organic fluorine compounds through C-F bond formation is still a highly desirable goal in synthetic organic chemistry. In this account, we review latest progresses in the area of catalytic enantioselective electrophilic fluorination of active methine compounds.

Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst

“…As part of the research program related to the development of synthetic methods for the catalytic carbon-carbon bond formations [ 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 ], we recently reported the organocatalytic conjugate addition reactions of α,β-unsaturated carbonyl compounds [ 51 , 52 , 53 ] and other Michael acceptors [ 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 ]. In this Communication, we wish to describe the enantioselective conjugate addition reaction of 3-substituted oxindoles with methyl vinyl ketone catalyzed by binaphthyl-modified bifunctional organocatalysts bearing both central and axial chiral elements.…”