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Iridium-Catalyzed Amidation of in Situ Prepared Silyl Ketene Acetals to Access α-Amino Esters

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Title
Iridium-Catalyzed Amidation of in Situ Prepared Silyl Ketene Acetals to Access α-Amino Esters
Author(s)
Yunyeong Gwon; Minhan Lee; Dongwook Kim; Sukbok Chang
Publication Date
2022-02
Journal
Organic Letters, v.24, no.4, pp.1088 - 1093
Publisher
American Chemical Society
Abstract
© Disclosed herein is a convenient Ir-catalyzed amidation of esters to access α-amido esters. Initially prepared silyl ketene acetals are directly employed, without separate purification, for subsequent amidation with an oxycarbonylnitrenoid precursor using the Cp*(LX)Ir(III) catalyst. The α-amidation was facile for both α-aryl and α-alkyl esters. Density functional theory studies revealed that the generation of a putative Ir-nitrenoid is facilitated by the chelation of the countercation additive during the N-O bond cleavage of the nitrene precursor.
URI
https://pr.ibs.re.kr/handle/8788114/11178
DOI
10.1021/acs.orglett.1c04376
ISSN
1523-7060
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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