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Free keywords:
Amino Acids; Carbocation; Carbonyl Compounds; Michael Acceptor; Umpolung
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 Cα-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.
