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基于[2.2]对环芳烷的平面手性碘芳烃的开发及其在β-酮酯的催化对映选择性氟化反应中的应用。

Development of Planar Chiral Iodoarenes Based on [2.2]Paracyclophane and Their Application in Catalytic Enantioselective Fluorination of β-Ketoesters.

机构信息

State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering , Nanjing University , 163 Xianlin Avenue , Nanjing 210023 , Jiangsu , China.

School of Environment and Chemical Engineering , Jiangsu University of Science and Technology , Zhenjiang 212003 , Jiangsu , China.

出版信息

Org Lett. 2018 May 4;20(9):2555-2558. doi: 10.1021/acs.orglett.8b00711. Epub 2018 Apr 13.

Abstract

The design and synthesis of novel planar chiral iodoarenes based on [2.2]paracyclophane is reported. A process of highly enantioselective oxidative fluorination of a β-ketoester with 3HF-EtN as a nucleophilic fluoride source mediated by these new hypervalent iodine catalysts has been developed. This represents the first highly enantioselective reaction catalyzed by planar chiral hypervalent iodine.

摘要

报告了基于[2.2]对环芳烷的新型平面手性碘芳烃的设计和合成。开发了一种新型高价碘催化剂介导的β-酮酯与 3HF-EtN 作为亲核氟源的高对映选择性氧化氟化过程。这代表了首例由平面手性高价碘催化的高对映选择性反应。

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