An Umpolung Strategy for the Synthesis of β-Aminoketones via Copper-Catalyzed Electrophilic Amination of Cyclopropanols

Zhishi Ye and Mingji Dai*

*Department of Chemistry and Center for Cancer Research, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States, Email: mjdaipurdue.edu

Z. Ye, M. Dai, Org. Lett., 2015, 17, 2190-2193.

DOI: 10.1021/acs.orglett.5b00828

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Abstract

A copper-catalyzed electrophilic amination of cyclopropanols with O-benzoyl-N,N-dialkylhydroxylamines enables the synthesis of various β-aminoketones via C-C bond cleavage and Csp³-N bond formation. The mild reaction conditions tolerate several functional groups including benzoate, tosylate, expoxide, and α,β-unsaturated carbonyls.

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Key Words

β-aminoketones

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ID: J54-Y2015