Construction of Chiral alpha-Amino Quaternary Stereogenic Centers via Phase-Transfer Catalyzed Enantioselective alpha-Alkylation of alpha-Amidomalonates
DC Field | Value | Language |
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dc.contributor.author | Ha, Min Woo | - |
dc.contributor.author | Lee, Myungmo | - |
dc.contributor.author | Choi, Sujee | - |
dc.contributor.author | Kim, Seek | - |
dc.contributor.author | Hong, Suckchang | - |
dc.contributor.author | Park, Yohan | - |
dc.contributor.author | Kim, Mi-hyun | - |
dc.contributor.author | Kim, Taek-Soo | - |
dc.contributor.author | Lee, Jihoon | - |
dc.contributor.author | Lee, Jae Kyun | - |
dc.contributor.author | Park, Hyeung-geun | - |
dc.date.available | 2020-02-28T09:46:28Z | - |
dc.date.created | 2020-02-06 | - |
dc.date.issued | 2015-03-20 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/10695 | - |
dc.description.abstract | An efficient enantioselective synthetic method for alpha-amido-alpha-alkylmalonates via phase-transfer catalytic alpha-alkylation was successfully developed. The alpha-alkylation of alpha-amidomalonates under phase-transfer catalytic conditions (50% KOH, toluene, -40 degrees C) in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded the corresponding alpha-amido-alpha-alkylmalonates in high chemical yields (up to 99%) and optical yields (up to 97% ee), which could be readily converted to versatile chiral intermediates bearing alpha-amino quaternary stereogenic centers. The synthetic potential of this methodology was demonstrated via the synthesis of chiral azlactone, oxazoline, and unnatural alpha-amino acid. | - |
dc.language | 영어 | - |
dc.language.iso | en | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.relation.isPartOf | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.subject | BETA-KETO-ESTERS | - |
dc.subject | ASYMMETRIC-SYNTHESIS | - |
dc.subject | ELECTROPHILIC AMINATION | - |
dc.subject | KETOESTERS | - |
dc.subject | ACID | - |
dc.subject | HYDRAZINATION | - |
dc.subject | TRISOXAZOLINE | - |
dc.title | Construction of Chiral alpha-Amino Quaternary Stereogenic Centers via Phase-Transfer Catalyzed Enantioselective alpha-Alkylation of alpha-Amidomalonates | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.description.journalClass | 1 | - |
dc.identifier.wosid | 000351558400035 | - |
dc.identifier.doi | 10.1021/jo502791d | - |
dc.identifier.bibliographicCitation | JOURNAL OF ORGANIC CHEMISTRY, v.80, no.6, pp.3270 - 3279 | - |
dc.identifier.scopusid | 2-s2.0-84925358844 | - |
dc.citation.endPage | 3279 | - |
dc.citation.startPage | 3270 | - |
dc.citation.title | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.citation.volume | 80 | - |
dc.citation.number | 6 | - |
dc.contributor.affiliatedAuthor | Kim, Mi-hyun | - |
dc.contributor.affiliatedAuthor | Kim, Taek-Soo | - |
dc.type.docType | Article | - |
dc.subject.keywordPlus | BETA-KETO-ESTERS | - |
dc.subject.keywordPlus | ASYMMETRIC-SYNTHESIS | - |
dc.subject.keywordPlus | ELECTROPHILIC AMINATION | - |
dc.subject.keywordPlus | KETOESTERS | - |
dc.subject.keywordPlus | ACID | - |
dc.subject.keywordPlus | HYDRAZINATION | - |
dc.subject.keywordPlus | TRISOXAZOLINE | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
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