Chiral acid-catalysed enantioselective C-H functionalization of toluene and its derivatives driven by visible light.

ABSTRACT: Toluene and its derivatives are petroleum-derived raw materials produced from gasoline by catalytic reformation. These abundant chemical feedstocks are commonly used as solvents in organic synthesis. The C(sp³)-H functionalization of these unactivated substrates has been widely used to directly introduce benzylic motifs into diverse molecules to furnish important compounds. Despite these advances, progress in asymmetric catalysis remains underdeveloped. Here, we report photoinduced radical-based enantioselective C(sp³)-C(sp³) coupling reactions of activated ketones with toluene and its derivatives by means of chiral acid catalysis. With a La(OTf)₃/pybox complex catalyst, a variety of chiral 3-hydroxy-3-benzyl-substituted 2-oxindoles, including ma

SUBMITTER: Li F 

PROVIDER: S-EPMC6467922 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature