Synthetic Utility of N-Benzoyloxyamides as an Alternative Precursor of Acylnitrenoids for gamma-Lactam Formation

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Described herein is the development of a new entry of acylnitrenoid precursors for gamma-lactam synthesis via an intramolecular C-H amidation reaction. Upon Ir catalysis, N-benzoyloxyamides serve as efficient substrates to afford 5-membered amides. Mechanistic studies revealed that the generation of a putative Ir-carbonylnitrenoid via N-O bond cleavage is facilitated by the chelation of countercations. This protocol offers a convenient and step-economic route to gamma-lactams starting from the corresponding carboxylic acids.
Publisher
AMER CHEMICAL SOC
Issue Date
2019-04
Language
English
Article Type
Article
Citation

ORGANIC LETTERS, v.21, no.8, pp.2808 - 2812

ISSN
1523-7060
DOI
10.1021/acs.orglett.9b00791
URI
http://hdl.handle.net/10203/262210
Appears in Collection
CH-Journal Papers(저널논문)
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