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有机催化氟代氧化吲哚对香豆素迈克尔受体的对映选择性加成反应。

Organocatalytic atroposelective fluorooxindole addition to coumarin Michael acceptors.

作者信息

Bouda Maria, Hana Grace E, Xhili Dea, Sripada Archita, Bertke Jeffery A, Wolf Christian

机构信息

Department of Chemistry, Georgetown University, Washington, D. C. 20057, USA.

出版信息

Chem Commun (Camb). 2025 May 22;61(43):7883-7886. doi: 10.1039/d5cc01166c.

DOI:10.1039/d5cc01166c
PMID:40314408
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12047072/
Abstract

Organocatalytic atropisomeric synthesis with fluorinated oxindoles and 4-halo-3-nitrocoumarins gives congested structures displaying a Csp-Csp chirality axis and an adjacent tetrasubstituted stereogenic carbon center with good yields, up to 97% ee and 41 : 1 dr. The scalable dehalogenative C-C bond formation is achieved under mild conditions with a commercially available urea catalyst.

摘要

使用氟化氧化吲哚和4-卤代-3-硝基香豆素进行有机催化阻转异构合成,可得到具有拥挤结构的产物,这些产物具有Csp-Csp手性轴和相邻的四取代立体中心,产率良好,对映体过量高达97%,非对映体比例为41:1。使用市售的脲催化剂在温和条件下可实现可扩展的脱卤碳-碳键形成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/993d/12047072/036e5c55e062/d5cc01166c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/993d/12047072/a79c3720bb12/d5cc01166c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/993d/12047072/c488aae4ba60/d5cc01166c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/993d/12047072/4b8d47627e30/d5cc01166c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/993d/12047072/036e5c55e062/d5cc01166c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/993d/12047072/a79c3720bb12/d5cc01166c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/993d/12047072/c488aae4ba60/d5cc01166c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/993d/12047072/4b8d47627e30/d5cc01166c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/993d/12047072/036e5c55e062/d5cc01166c-s4.jpg

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