Synthesis of Lactams via a Chiral Phosphoric Acid-Catalyzed Aniline Cyclization
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.
Authors
- Kimberly S. Petersen (ORCID: https://orcid.org/0000-0002-5020-3549)
- Shubin Liu (ORCID: https://orcid.org/0000-0001-9331-0427)
- Abigail H. Horchar
- Jonathan E. Dean
- Alexander R. Lake
- Tiana R. Lillevig
- Jessica E. Carsley
Institutions
- University of North Carolina at Chapel Hill (US)
- University of North Carolina at Greensboro (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-08-09
- DOI
- https://doi.org/10.1021/acs.joc.4c01060
- Citations
- 2
- Primary Topic
- Chemical synthesis and alkaloids
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- National Science Foundation
- University of North Carolina at Greensboro
- National Institute of General Medical Sciences
- Division of Graduate Education
- Division of Chemistry