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α‐Thianthrenium Carbonyl Species: The Equivalent of an α‐Carbonyl Carbocation

Hao Jia, Tobias Ritter

2022Angewandte Chemie International Edition55 citationsDOIOpen Access PDF

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
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