α-Thianthrenium Carbonyl Species: The Equivalent of an α-Carbonyl Carbocation.

ABSTRACT: Here we report an α-thianthrenium carbonyl species, as the equivalent of an α-carbonyl carbocation, which is generated by the radical conjugate addition of a trifluoromethyl thianthrenium salt to Michael acceptors. The reactivity allows for the synthesis of C^α -tetrasubstituted α- and β-amino acid analogues via a Ritter reaction by addition of acetonitrile. Addition of hydroxide, methoxide, and even fluoride can afford α-heteroatom substituted α-phenylpropanoates.

SUBMITTER: Jia H 

PROVIDER: S-EPMC9804271 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature