On the Origin of Rh-Catalyzed Selective Ring-Opening Amidation of Substituted Cyclopropanols to Access beta(2)-Amino Ketones

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beta(2)-Amino carbonyls, an alpha-substituted beta-amino scaffold, hold a prominent place in the development of new pharmaceuticals and peptidomimetics. Herein, we report a highly efficient Rh-catalyzed ring-opening amidation of substituted cyclopropanols, which turned out to serve as a linchpin for the selective synthesis of beta(2)-amino ketones to outcompete the formation of beta(3)-isomers. Instead of the generally accepted rationale to consider steric factors for the beta(2)-selectivity, orbital interaction was elucidated to play a more critical role in the amidative ring-opening of cyclopropanols to generate the key Rh-C intermediate. Subsequent inner-sphere acylnitrene transfer was achieved in excellent efficiency (TON > 5000) by using readily accessible dioxazolones as the amino source to afford beta(2)-amino ketones with broad applicability.
Publisher
AMER CHEMICAL SOC
Issue Date
2022-03
Language
English
Article Type
Article
Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.144, no.8, pp.3667 - 3675

ISSN
0002-7863
DOI
10.1021/jacs.1c12934
URI
http://hdl.handle.net/10203/292590
Appears in Collection
CH-Journal Papers(저널논문)
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