Imine Directed Cp*Rh^III -Catalyzed N-H Functionalization and Annulation with Amino Amides, Aldehydes, and Diazo Compounds.

ABSTRACT: A multicomponent annulation that proceeds by imine directed Cp*Rh^III -catalyzed N-H functionalization is disclosed. The transformation affords piperazinones displaying a range of functionality and is the first example of transition metal-catalyzed multicomponent N-H functionalization. A broad range of readily available α-amino amides, including those derived from glycine, α-substituted, and α,α-disubstituted amino acids, were effective inputs and enabled the incorporation of a variety of amino acid side chains with minimal racemization. Branched and unbranched alkyl aldehydes and various stabilized diazo compounds were also efficient reactants. The piperazinone products were further modified through efficient transformations. Mechanistic studies, including X-ray crystallographic

SUBMITTER: Zoll AJ 

PROVIDER: S-EPMC9805510 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature