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Enantioselective Access to Spirolactams via Nitrenoid Transfer Enabled by Enhanced Noncovalent Interactions

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Title
Enantioselective Access to Spirolactams via Nitrenoid Transfer Enabled by Enhanced Noncovalent Interactions
Author(s)
Euijae Lee; Yeongyu Hwang; Yeong Bum Kim; Dongwook Kim; Sukbok Chang
Publication Date
2021-05
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.143, no.17, pp.6363 - 6369
Publisher
AMER CHEMICAL SOC
Abstract
Described herein is the Ir-catalyzed enantioselective access to chiral spirolactam products via the nitrenoid transfer to aromatic ipso-carbons. The key strategy for precise stereocontrol is to enhance the secondary attractive and repulsive interactions between the chiral catalyst and substrates by the introduction of a traceless O-silyl achiral auxiliary, thus effectively differentiating two prochiral faces of arenol-derived 1,4,2-dioxazol-5-one substrates.
URI
https://pr.ibs.re.kr/handle/8788114/9695
DOI
10.1021/jacs.1c02550
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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