α‐Thianthrenium Carbonyl Species: The Equivalent of an α‐Carbonyl Carbocation
Hao Jia, Tobias Ritter
Abstract
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.
Topics & Concepts
CarbocationChemistryMedicinal chemistrySulfur-Based Synthesis TechniquesAsymmetric Synthesis and CatalysisRadical Photochemical Reactions