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Iridium-Catalyzed Enantioselective C(sp3)-H Amidation Controlled by Attractive Noncovalent Interactions

Hao Wang, Yoonsu Park, Ziqian Bai, Sukbok Chang*, Gang He*, Gong Chen*

*Korea Advanced Institute of Science and Technology, Daejeon 34141, Republic of Korea; Nankai University, Tianjin 300071, China, Email: sbchangkaist.ac.kr, hegangnankai.edu.cn, gongchennankai.edu.cn

H. Wang, Y. Park, Z. Bai, S. Chang, G. He, G. Chen, J. Am. Chem. Soc., 2019, 141, 7194-7201.

DOI: 10.1021/jacs.9b02811


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Abstract

A highly enantioselective Ir(III)-catalyzed intramolecular C(sp3)-H amidation reaction of dioxazolone substrates provides optically enriched γ-lactams using an α-amino-acid-based chiral ligand. This reaction proceeds with excellent efficiency and with outstanding enantioselectivity for both activated and unactivated alkyl C(sp3)-H bonds under very mild conditions.

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Key Words

γ-lactams


ID: J48-Y2019