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使用二氟甲磺酰基高价碘𬭩叶立德对基于茚满酮的β-酮酯进行不对称亲电二氟甲硫基化反应。

Asymmetric Electrophilic Difluoromethylthiolation of Indanone-Based β-Keto Esters Using Difluoromethanesulfonyl Hypervalent Iodonium Ylides.

机构信息

Department of Nanopharmaceutical Sciences, Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

CNRS, UMR 6014 COBRA, Normandie Université, 1 Rue Tesnière, F-76821 Mont-Saint-Aignan Cedex, France.

出版信息

Molecules. 2019 Jan 9;24(2):221. doi: 10.3390/molecules24020221.

DOI:10.3390/molecules24020221
PMID:30634428
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6359606/
Abstract

The first electrophilic diastereoselective direct introduction of the difluoromethylthio group is described. We used a chiral auxiliary-based approach to illustrate the versatility of our recently developed difluoromethanesulfonyl hypervalent iodonium ylide reagents for the difluoromethylthiolation of indanone-based β-keto esters. Chiral SCF₂H-featuring compounds were obtained in up to 93% ee value.

摘要

首次描述了手性辅助的一氟甲基硫基的亲电立体选择性直接引入。我们采用基于手性辅基的方法,展示了我们最近开发的二氟甲磺酰基高碘𬭩叶立德试剂在基于茚酮的β-酮酯的二氟甲硫基化反应中的多功能性。含有手性 SCF₂H 的化合物以高达 93%的对映体过量值(ee 值)得到。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9f49/6359606/5dd455cd1bfc/molecules-24-00221-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9f49/6359606/f2467948ed26/molecules-24-00221-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9f49/6359606/09ea1aa1315a/molecules-24-00221-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9f49/6359606/5dd455cd1bfc/molecules-24-00221-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9f49/6359606/f2467948ed26/molecules-24-00221-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9f49/6359606/09ea1aa1315a/molecules-24-00221-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9f49/6359606/5dd455cd1bfc/molecules-24-00221-sch003.jpg

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Chiral Selenide-Catalyzed Enantioselective Allylic Reaction and Intermolecular Difunctionalization of Alkenes: Efficient Construction of C-SCF Stereogenic Molecules.
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