Enantioselective Synthesis of (R)-Sitagliptin via Phase-Transfer Catalytic aza-Michael Addition
DC Field | Value | Language |
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dc.contributor.author | Oh, Daehyun | - |
dc.contributor.author | Lee, Jaeyong | - |
dc.contributor.author | Yang, Sehun | - |
dc.contributor.author | Jung, So Hyun | - |
dc.contributor.author | Kim, Mihyun | - |
dc.contributor.author | Lee, Geumwoo | - |
dc.contributor.author | Park, Hyeung-Geun | - |
dc.date.accessioned | 2024-04-25T11:30:20Z | - |
dc.date.available | 2024-04-25T11:30:20Z | - |
dc.date.issued | 2024-03 | - |
dc.identifier.issn | 2470-1343 | - |
dc.identifier.issn | 2470-1343 | - |
dc.identifier.uri | https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/91045 | - |
dc.description.abstract | The highly enantioselective synthesis of (R)-sitagliptin has been achieved through a series of key steps, including the aza-Michael addition and Baeyer-Villiger oxidation. The enantioselective aza-Michael addition involved the reaction of tert-butyl β-naphthylmethoxycarbamate with (E)-1-(4-methoxyphenyl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one, utilizing a quinine-derived C(9)-urea ammonium catalyst under phase-transfer catalytic conditions. The aza-Michael addition successfully introduced chirality to the amine in (R)-sitagliptin with 96% ee. The subsequent Baeyer-Villiger oxidation of the aza-Michael adduct led to the formation of 4-methoxyphenyl ester. Hydrolysis and amide coupling were then employed to construct the amide moiety. Further deprotections were performed to complete the synthesis of (R)-sitagliptin (7 steps, 41%, 96% ee). © 2024 The Authors. Published by American Chemical Society | - |
dc.format.extent | 11 | - |
dc.language | 영어 | - |
dc.language.iso | ENG | - |
dc.publisher | American Chemical Society | - |
dc.title | Enantioselective Synthesis of (R)-Sitagliptin via Phase-Transfer Catalytic aza-Michael Addition | - |
dc.type | Article | - |
dc.identifier.wosid | 001189800200001 | - |
dc.identifier.doi | 10.1021/acsomega.3c10080 | - |
dc.identifier.bibliographicCitation | ACS Omega, v.9, no.13, pp 15328 - 15338 | - |
dc.description.isOpenAccess | Y | - |
dc.identifier.scopusid | 2-s2.0-85188526315 | - |
dc.citation.endPage | 15338 | - |
dc.citation.startPage | 15328 | - |
dc.citation.title | ACS Omega | - |
dc.citation.volume | 9 | - |
dc.citation.number | 13 | - |
dc.type.docType | Article | - |
dc.publisher.location | 미국 | - |
dc.subject.keywordPlus | ASYMMETRIC-SYNTHESIS | - |
dc.subject.keywordPlus | IV INHIBITOR | - |
dc.subject.keywordPlus | SITAGLIPTIN | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
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