Work

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

Year: 2026

Type: article

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.

Source: UNC Libraries

DOI: 10.17615/gsbs-8855

Authors: Dean, Jonathan E., Carsley, Jessica E., Lillevig, Tiana R., Horchar, Abigail H., Liu, Shubin, Petersen, Kimberly S., Lake, Alexander R.

Institution: University of North Carolina at Chapel Hill

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Directorate for Mathematical and Physical Sciences, Directorate for STEM Education, National Institute of General Medical Sciences, Division of Graduate Education, Division of Chemistry, National Center for Complementary and Integrative Health

OpenAlex ID: W7151894508

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