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通过铜催化的不对称共轭加成反应，由CF和CH取代基诱导形成手性全碳季碳中心。

Creation of a Chiral All-Carbon Quaternary Center Induced by CF and CH Substituents via Cu-Catalyzed Asymmetric Conjugate Addition.

作者信息

Yamamoto Taiyo, Asakura Masayuki, Yamanomoto Ken, Shibata Takanori, Endo Kohei

机构信息

Department of Chemistry, Faculty of Science, Tokyo University of Science, Shinjuku, Tokyo 162-8601, Japan.

Department of Chemistry and Biochemistry, Graduate School of Science and Technology, Waseda University, Shinjuku, Tokyo 169-8555, Japan.

出版信息

Org Lett. 2024 Jun 28;26(25):5312-5317. doi: 10.1021/acs.orglett.4c01691. Epub 2024 Jun 13.

DOI:10.1021/acs.orglett.4c01691
PMID:38869935
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11217942/
Abstract

Cu-catalyzed asymmetric construction of a chiral quaternary center bearing CH and CF groups was achieved with high to excellent enantioselectivity using our originally developed ligands. The asymmetric conjugate addition of MeAl to β-CF-substituted enones and unsaturated ketoesters proceeded efficiently. The use of unsaturated ketoesters gives optically active furanones in high yields with high enantioselectivities. The perfluoroalkyl-substituted enone does not seem to be favorable in the present reaction.

摘要

使用我们最初开发的配体，以高至优异的对映选择性实现了铜催化的含CH和CF基团的手性季碳中心的不对称构建。MeAl对β-CF取代的烯酮和不饱和酮酯的不对称共轭加成反应高效进行。使用不饱和酮酯能以高收率和高对映选择性得到光学活性的呋喃酮。在本反应中，全氟烷基取代的烯酮似乎不太有利。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/0b13c758d274/ol4c01691_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/0da16f6e54e9/ol4c01691_0004.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/affd0f1290f3/ol4c01691_0006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/698b264651af/ol4c01691_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/2926c9c3998f/ol4c01691_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/416028d84b44/ol4c01691_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/0b13c758d274/ol4c01691_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/0da16f6e54e9/ol4c01691_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/09ea664bf53c/ol4c01691_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/affd0f1290f3/ol4c01691_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/7592bd76d578/ol4c01691_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/698b264651af/ol4c01691_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/2926c9c3998f/ol4c01691_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/416028d84b44/ol4c01691_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d22/11217942/0b13c758d274/ol4c01691_0011.jpg

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