Synthesis of Lactams via a Chiral Phosphoric Acid-Catalyzed Aniline Cyclization.

ABSTRACT: The enantioenriched lactams disclosed in this work are synthesized concisely in four steps. In the penultimate reaction, a benzylamine species complexes with a chiral phosphoric acid to produce benzo-fused δ-lactams equipped with an all-carbon quaternary stereocenter. Partial and full reductions were carried out on the ester and amide moieties, and a Suzuki-Miyaura cross-coupling expanded the molecule from the aromatic ring. Finally, our method was successful at a >1 g scale, indicating that the method has important practical use.

SUBMITTER: Horchar AH 

PROVIDER: S-EPMC11382273 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature