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분자활성촉매반응연구단
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Enantioselective Access to β-Amino Carbonyls via Ni-Catalyzed Formal Olefin Hydroamidation

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Title
Enantioselective Access to β-Amino Carbonyls via Ni-Catalyzed Formal Olefin Hydroamidation
Author(s)
Lyu, Xiang; Jung, Hoimin; Kim, Dongwook; Chang, Sukbok
Publication Date
2024-05
Journal
Journal of the American Chemical Society, v.146, no.21, pp.14745 - 14753
Publisher
American Chemical Society
Abstract
We herein describe a Ni-catalyzed formal hydroamidation of readily available α,β-unsaturated carbonyl compounds to afford valuable chiral β-amino acid derivatives (up to >99:1 e.r.) using dioxazolones as a robust amino source. A wide range of alkyl-substituted olefins conjugated to esters, amides, thioesters, and ketones were successfully amidated at the β-position with excellent enantioselectivity for the first time. Combined experimental and computational mechanistic studies supported our working hypothesis that this unconventional β-amidation of unsaturated carbonyl substrates can be attributed to the polar-matched migratory olefin insertion of an (amido)(Cl)NiII intermediate, in situ generated from the dioxazolone precursor. © 2024 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/15282
DOI
10.1021/jacs.4c02497
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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