Synthesis of polycyclic aminal heterocycles via decarboxylative cyclisation of dipeptide derivatives

Abstract

An oxidative-decarboxylative intramolecular cyclisation of dipeptide derivatives is reported. This transformation is promoted by phenyl iodine (III) diacetate (PIDA) in combination with BF3·OEt2. The reaction gives access to a variety...

Progress on the Synthesis and Applications of Aminals: Scaffolds for Molecular Diversity

“…The latter can either be oxidized to afford the iminium ion. [78][79][80][81][82][83] The former, serving as one of the few examples of applying such strategies in total synthesis, was applied by Rippel et al 84 in the racemic synthesis of Cernumidine.…”

Transformations based on direct excitation of hypervalent iodine(iii) reagents

“…A similar reactivity was also observed by the Waser group in their report of intramolecular cyclisation of dipeptide derivatives. 46 However, for their substrates light input was not required.…”

C(sp3)–H Ritter amination by excitation of in situ generated iodine(iii)–BF3 complexes

“…Recently, we found that visible light excitation of phenyliodine( iii ) dicarboxylate–BF 3 complexes leads to a decarboxylative Ritter amination via carbenium intermediates (Scheme 1b). 6 The strategy is quite unique in a sense that it does not require any photocatalyst to mediate the electron transfers to obtain the charged intermediates. 7 Moreover, it is based on simple commercial reagents, without the need for any sophisticated oxidizing agents.…”