American Chemical Society
ol9b02267_si_001.pdf (9.27 MB)

Copper-Catalyzed Enantioselective Ring-Opening of Cyclic Diaryliodoniums and O‑Alkylhydroxylamines

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journal contribution
posted on 2019-07-30, 15:35 authored by Qigang Li, Mingkai Zhang, Shuming Zhan, Zhenhua Gu
A preparation of 2-hydroxyamino-2′-iodobiaryls via the Cu-catalyzed enantioselective ring-opening reaction of cyclic diaryliodonium salts with O-alkylhydroxylamines is reported. 3,5-Di­(tert-butyl)­phenyl bis­(oxazoline) was found to be the optimal ligand, and up to 99% ee values were achieved. The use of CaO as the base dramatically improved the yields and inhibited the side reactions. Finally, synthetic applications of these hydroxylamines were briefly demonstrated.