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Access to β-Lactams via Iron-Catalyzed Olefin Oxyamidation Enabled by the π-Accepting Phthalocyanine Ligand

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Title
Access to β-Lactams via Iron-Catalyzed Olefin Oxyamidation Enabled by the π-Accepting Phthalocyanine Ligand
Author(s)
Jeonguk Kweon; Dongwook Kim; Seungju Kang; Sukbok Chang
Publication Date
2022-02
Journal
Journal of the American Chemical Society, v.144, no.4, pp.1872 - 1880
Publisher
American Chemical Society
Abstract
Herein, we report the development of an iron-catalyzed olefin oxyamidation by utilizing tethered dioxazolones as the nitrenoid precursor to produce valuable β-lactam scaffolds. Mechanistic studies revealed that a relatively strong π-accepting ability of the phthalocyanine ligand is critical in generating the key triplet iron-imidyl radical intermediate to enable the 4-exo-trig-lactamization with the incorporation of oxygen nucleophiles in high diastereoselectivity. This cyclization approach was readily extended to the highly efficient γ-lactam synthesis (TON > 300).
URI
https://pr.ibs.re.kr/handle/8788114/11193
DOI
10.1021/jacs.1c12125
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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