DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lee, Minhan | ko |
dc.contributor.author | Heo, Joon | ko |
dc.contributor.author | Kim, Dongwook | ko |
dc.contributor.author | Chang, Sukbok | ko |
dc.date.accessioned | 2022-04-13T06:51:45Z | - |
dc.date.available | 2022-04-13T06:51:45Z | - |
dc.date.created | 2022-04-11 | - |
dc.date.created | 2022-04-11 | - |
dc.date.created | 2022-04-11 | - |
dc.date.issued | 2022-03 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.144, no.8, pp.3667 - 3675 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/292590 | - |
dc.description.abstract | 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. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | On the Origin of Rh-Catalyzed Selective Ring-Opening Amidation of Substituted Cyclopropanols to Access beta(2)-Amino Ketones | - |
dc.type | Article | - |
dc.identifier.wosid | 000773646200039 | - |
dc.identifier.scopusid | 2-s2.0-85125294876 | - |
dc.type.rims | ART | - |
dc.citation.volume | 144 | - |
dc.citation.issue | 8 | - |
dc.citation.beginningpage | 3667 | - |
dc.citation.endingpage | 3675 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/jacs.1c12934 | - |
dc.contributor.localauthor | Chang, Sukbok | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | ENANTIOSELECTIVE CONJUGATE ADDITION | - |
dc.subject.keywordPlus | MANNICH-TYPE REACTIONS | - |
dc.subject.keywordPlus | BETA-AMINO KETONES | - |
dc.subject.keywordPlus | C-H AMIDATION | - |
dc.subject.keywordPlus | ASYMMETRIC-SYNTHESIS | - |
dc.subject.keywordPlus | VINYL AZIDES | - |
dc.subject.keywordPlus | BOND | - |
dc.subject.keywordPlus | ACID | - |
dc.subject.keywordPlus | IMINES | - |
dc.subject.keywordPlus | HYDROGENATION | - |
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