A stereodivergent multicomponent approach for the synthesis of C-N atropisomeric peptide analogues.

ABSTRACT: A four-component Ugi reaction is described for the stereoselective synthesis of novel C-N atropisomeric peptide analogues. Using this approach, a combination of simple, readily available starting materials (ortho-substituted anilines, aldehydes, carboxylic acids and isocyanides) could be combined to access complex products possessing both central and axial chirality in up to 92% yield and >95 : 5 d.r. Variation of the reaction temperature enabled the development of stereodivergent reactions capable of selectively targeting either diastereoisomer of a desired product from a single set of starting materials with high levels of stereocontrol. Detailed experimental and computational studies have been performed to probe the reaction mechanism and stereochemical outcome of these reactions

SUBMITTER: Roper NJ 

PROVIDER: S-EPMC11418089 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature