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Regio- and Enantioselective Catalytic δ-C-H Amidation of Dioxazolones Enabled by Open-Shell Copper-Nitrenoid Transfer

Suhyeon Kim, Se Lin Song, Jianbo Zhang, Dongwook Kim, Sungwoo Hong and Sukbok Chang*

*Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, South Korea, Email: sbchangkaist.ac.kr

S. Kim, S. L. Song, J. Zhang, D. Kim, S. Hong, S. Chang, J. Am. Chem. Soc., 2023, 145, 16238-16248.

DOI: 10.1021/jacs.3c05258


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Abstract

An asymmetric δ-C(sp3)-H amidation of dioxazolones using a Cu(I) precursor with a chiral bisoxazoline ligand as catalyst provides six-membered lactams with high to excellent regio- and enantioselectivity.

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proposed mechanism


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Key Words

δ-lactams


ID: J48-Y2023