ArticleThe Journal of organic chemistry2024
Synthesis of Lactams via a Chiral Phosphoric Acid-Catalyzed Aniline Cyclization.
Abigail H Horchar, Jonathan E Dean, Alexander R Lake, Jessica E Carsley, Tiana R Lillevig, Shubin Liu, Kimberly S Petersen
Abstract read
In one paragraphArticle in The Journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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2 · The registryThe trial behind it
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4 · The recordCorrections and comments
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5 · Who and what moneyAuthors and funding
7 authors.
Abigail H HorcharDepartment of Chemistry and Biochemistry, The University of North Carolina at Greensboro, 301 McIver Street, Greensboro, North Carolina 27412, United States.
Jonathan E DeanDepartment of Chemistry and Biochemistry, The University of North Carolina at Greensboro, 301 McIver Street, Greensboro, North Carolina 27412, United States.
Alexander R LakeDepartment of Chemistry and Biochemistry, The University of North Carolina at Greensboro, 301 McIver Street, Greensboro, North Carolina 27412, United States.
Jessica E CarsleyDepartment of Chemistry and Biochemistry, The University of North Carolina at Greensboro, 301 McIver Street, Greensboro, North Carolina 27412, United States.
Tiana R LillevigDepartment of Chemistry and Biochemistry, The University of North Carolina at Greensboro, 301 McIver Street, Greensboro, North Carolina 27412, United States.
Shubin LiuDepartment of Chemistry, The University of North Carolina at Chapel Hill, 125 South Road, Chapel Hill, North Carolina 27514, United States.ORCID 0000-0001-9331-0427 Kimberly S PetersenDepartment of Chemistry and Biochemistry, The University of North Carolina at Greensboro, 301 McIver Street, Greensboro, North Carolina 27412, United States.ORCID 0000-0002-5020-3549 Funding
Predoctoral Training: Innovative Technologies for Natural Products and Integrative Medicine ResearchT32AT008938 · NCCIH · UNIVERSITY OF NORTH CAROLINA GREENSBORO · PI Nadja B Cech, Jonathan Rodi Chekan · 2016 to 2026
$1.6MUNC Greensboro MARC USTAR Engage, Sustain, and PrepareT34GM113860 · NIGMS · UNIVERSITY OF NORTH CAROLINA GREENSBORO · PI GRAVES, JOSEPH LEWIS, HERR, DANIEL J · 2017 to 2021
$1.4MUNC-Greensboro U-RISE: Engage, Sustain, and Prepare Future PhD Biomedical ScientistsT34GM149494 · NIGMS · UNIVERSITY OF NORTH CAROLINA GREENSBORO · PI MCLEAN, BRYAN STEPHEN, OBARE, SHERINE O. · 2023 to 2024
$534kStereoselective Synthesis of Biologically Relevant Heterocycles via Brønsted Acid CatalysisR15GM141981 · NIGMS · UNIVERSITY OF NORTH CAROLINA GREENSBORO · PI PETERSEN, KIMBERLY SUE · 2021 to 2021
$396kNCCIH NIH HHS T32 AT008938NIGMS NIH HHS R15 GM141981NIGMS NIH HHS T34 GM113860NIGMS NIH HHS T34 GM149494
6 · The paper itselfAbstract
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.
Identifiers
PMID39120519
PMCPMC11382273
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