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铜催化的通过五元环状二芳基碘鎓的硫代环开反应的对映选择性非对映异构体合成。

Cu-Catalyzed Enantioselective Atropisomer Synthesis via Thiolative Ring Opening of Five-Membered Cyclic Diaryliodoniums.

机构信息

Department of Chemistry, Center for Excellence in Molecular Synthesis, and Hefei National Laboratory for Physical Sciences at the Microscale , University of Science and Technology of China , 96 Jinzhai Road , Hefei , Anhui 230026 , P.R. China.

出版信息

Org Lett. 2018 Sep 21;20(18):5779-5783. doi: 10.1021/acs.orglett.8b02477. Epub 2018 Sep 7.

Abstract

A Cu-catalyzed asymmetric thiolative ring opening reaction of five-membered diaryliodonium salts and potassium thioates for the synthesis of atropisomeric 2'-iodo-[1,1'-biphenyl]-2-yl thioates was realized. The optimal catalytic system, Cu(CHCN)PF/(Ph)-bis(oxazoline), showed the best performance with respect to both yields and stereocontrol. Finally, the utility of these products was briefly demonstrated by the synthesis of an axially chiral P,S-ligand.

摘要

实现了铜催化的五元二芳基碘鎓盐与硫代钾盐的不对称硫叶立德开环反应,用于合成非对应异构体的 2'-碘-[1,1'-联苯]-2-基硫代酯。最优的催化体系为 Cu(CHCN)PF/(Ph)-双(恶唑啉),在产率和立体控制方面都表现出最佳性能。最后,通过合成轴手性的 P,S-配体,初步展示了这些产物的实用性。

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