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분자활성촉매반응연구단
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Visible-Light-Promoted Enantioselective α-Amidation of Aldehydes by Harnessing Organo-Iron Dual Catalysis

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Title
Visible-Light-Promoted Enantioselective α-Amidation of Aldehydes by Harnessing Organo-Iron Dual Catalysis
Author(s)
Soumyadip Hore; Jiwoo Jeong; Dongwook Kim; Sukbok Chang
Publication Date
2024-08
Journal
Journal of the American Chemical Society, v.146, no.32, pp.22172 - 22179
Publisher
American Chemical Society
Abstract
The strategic integration of organocatalysis with transition-metal catalysis to achieve otherwise unattainable stereoselective transformations may serve as a powerful synthetic tool. Herein, we present a synthetically versatile alpha-amidation of aldehydes by leveraging dual iron and chiral enamine catalysis in an enantioselective manner (up to >99:1 er). Experimental and computational studies have led us to propose a new mechanistic platform, wherein visible-light-promoted LMCT generates [Fe(II)Cl-3 (-)], which effectively activates dioxazolones to form an iron-acylnitrenoid radical that inserts into chiral enamine intermediates.
URI
https://pr.ibs.re.kr/handle/8788114/15521
DOI
10.1021/jacs.4c07884
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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