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 wer...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-09, Vol.89 (17), p.12725-12738
Main Authors: Horchar, Abigail H., Dean, Jonathan E., Lake, Alexander R., Carsley, Jessica E., Lillevig, Tiana R., Liu, Shubin, Petersen, Kimberly S.
Format: Article
Language:English
Subjects:
aniline
benzylamines
lactams
organic chemistry
phosphoric acid
species
Suzuki reaction
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Summary: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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01060