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On the Origin of Rh-Catalyzed Selective Ring-Opening Amidation of Substituted Cyclopropanols to Access β2-Amino Ketones

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Title
On the Origin of Rh-Catalyzed Selective Ring-Opening Amidation of Substituted Cyclopropanols to Access β2-Amino Ketones
Author(s)
Minhan Lee; Joon Heo; Dongwook Kim; Sukbok Chang
Publication Date
2022-03
Journal
Journal of the American Chemical Society, v.144, no.8, pp.3667 - 3675
Publisher
American Chemical Society
Abstract
© β2-Amino carbonyls, an α-substituted β-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 β2-amino ketones to outcompete the formation of β3-isomers. Instead of the generally accepted rationale to consider steric factors for the β2-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 β2-amino ketones with broad applicability.
URI
https://pr.ibs.re.kr/handle/8788114/11253
DOI
10.1021/jacs.1c12934
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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