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

Qigang Li; Mingkai Zhang; Shuming Zhan; Zhenhua Gu

doi:10.1021/acs.orglett.9b02267

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

Org Lett. 2019 Aug 16;21(16):6374-6377. doi: 10.1021/acs.orglett.9b02267. Epub 2019 Jul 30.

Authors

Qigang Li¹, Mingkai Zhang¹, Shuming Zhan¹, Zhenhua Gu¹

Affiliation

¹ 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.

PMID: 31361495
DOI: 10.1021/acs.orglett.9b02267

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't