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通过手性磷酸催化苯胺环化合成内酰胺。

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

作者信息

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

机构信息

Department of Chemistry and Biochemistry, The University of North Carolina at Greensboro, 301 McIver Street, Greensboro, North Carolina 27412, United States.

Department of Chemistry, The University of North Carolina at Chapel Hill, 125 South Road, Chapel Hill, North Carolina 27514, United States.

出版信息

J Org Chem. 2024 Sep 6;89(17):12725-12738. doi: 10.1021/acs.joc.4c01060. Epub 2024 Aug 9.

DOI:10.1021/acs.joc.4c01060
PMID:39120519
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11382273/
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.

摘要

本研究中所披露的对映体富集内酰胺通过四步简洁合成。在倒数第二步反应中，苄胺类与手性磷酸络合，生成带有全碳季立体中心的苯并稠合δ-内酰胺。对酯基和酰胺基进行了部分还原和完全还原，并且通过铃木-宫浦交叉偶联反应从芳环扩展了分子。最后，我们的方法在大于1 g规模上取得成功，表明该方法具有重要的实际用途。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/949c/11382273/d4f36e843795/jo4c01060_0008.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/949c/11382273/d4f36e843795/jo4c01060_0008.jpg

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Org Biomol Chem. 2022 Apr 13;20(15):3160-3173. doi: 10.1039/d2ob00289b.
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Intramolecular Hydrogen Atom Transfer Hydroarylation of Alkenes toward δ-Lactams Using Cobalt-Photoredox Dual Catalysis.钴-光氧化还原双催化烯烃的分子内氢原子转移氢芳基化反应合成 δ-内酰胺。
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