JOURNAL ARTICLE

Cu-Catalyzed Enantioselective Atropisomer Synthesis\nvia Thiolative Ring Opening of Five-Membered Cyclic Diaryliodoniums

Mengqing Hou (4249309)Ruixian Deng (1829407)Zhenhua Gu (469659)

Year: 2018 Journal:   OPAL (Open@LaTrobe) (La Trobe University)   Publisher: La Trobe University

Abstract

A Cu-catalyzed asymmetric thiolative\nring opening reaction of five-membered\ndiaryliodonium salts and potassium thioates for the synthesis of atropisomeric\n2′-iodo-[1,1′-biphenyl]-2-yl thioates was realized.\nThe optimal catalytic system, Cu­(CH<sub>3</sub>CN)<sub>4</sub>PF<sub>6</sub>/(Ph)-bis­(oxazoline), showed the best performance with respect\nto both yields and stereocontrol. Finally, the utility of these products\nwas briefly demonstrated by the synthesis of an axially chiral <i>P,S</i>-ligand.

Keywords:
Enantioselective synthesis Atropisomer Ring (chemistry) Catalysis Yield (engineering) Axial symmetry Stereoselectivity

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