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Highly enantioselective phase‐transfer catalytic α‐alkylation of α‐tert‐butoxycarbonyllactams: Construction of β‐quaternary chiral pyrrolidine and piperidine systems : Highly enantioselective phase-transfer catalytic alpha-alkylation of alpha-tert-butoxycarbonyllactams: Construction of beta-quaternary chiral pyrrolidine and piperidine systems
DC Field | Value | Language |
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dc.contributor.author | Park, Yohan | - |
dc.contributor.author | Lee, Young Ju | - |
dc.contributor.author | Hong, Suck Chang | - |
dc.contributor.author | Kim, Mi-hyun | - |
dc.contributor.author | Lee, Myungmo | - |
dc.contributor.author | Kim, Taek-Soo | - |
dc.contributor.author | Lee, Jae Kyun | - |
dc.contributor.author | Jew, Sang-sup | - |
dc.contributor.author | Park, Hyeung-geun | - |
dc.date.accessioned | 2024-05-14T07:19:01Z | - |
dc.date.available | 2024-05-14T07:19:01Z | - |
dc.date.created | 2017-11-15 | - |
dc.date.issued | 2011-12 | - |
dc.identifier.citation | Advanced Synthesis and Catalysis, Vol.353 No.18, pp.3313-3318 | - |
dc.identifier.issn | 1615-4150 | - |
dc.identifier.uri | https://hdl.handle.net/10371/202033 | - |
dc.description.abstract | A new enantioselective alpha-alkylation of alpha-tert-butoxycarbonyllactams for the construction of beta-quaternary chiral pyrrolidine and piperidine core systems is reported. alpha-Alkylations of N-methyl-alpha-tert-butoxycarbonylbutyrolactam and N-diphenylmethyl-alpha-tert-butoxycarbonylvalerolactam under phase-transfer catalytic conditions (solid potassium hydroxide, toluene, -40 degrees C) in the presence of (S,S)-3,4,5-trifluorophenyl-3,3',5,5'-tetrahydro-2,6-bis(3,4,5-trifluorophenyl)-4,4'-spirobi[4H-dinaphth[2,1-c:1',2'-e]azepinium] bromide [(S,S)-NAS Br] (5 mol%) afforded the corresponding alpha-alkyl-alpha-tert-butoxycarbonyllactams in very high chemical (up to 99%) and optical yields (up to 98% ee). Our new catalytic systems provide attractive synthetic methods for pyrrolidine- and piperidine-based alkaloids and chiral intermediates with beta-quaternary carbon centers. | - |
dc.language | 영어 | - |
dc.publisher | John Wiley & Sons Ltd. | - |
dc.title | Highly enantioselective phase‐transfer catalytic α‐alkylation of α‐tert‐butoxycarbonyllactams: Construction of β‐quaternary chiral pyrrolidine and piperidine systems | - |
dc.title.alternative | Highly enantioselective phase-transfer catalytic alpha-alkylation of alpha-tert-butoxycarbonyllactams: Construction of beta-quaternary chiral pyrrolidine and piperidine systems | - |
dc.type | Article | - |
dc.identifier.doi | 10.1002/adsc.201100542 | - |
dc.citation.journaltitle | Advanced Synthesis and Catalysis | - |
dc.identifier.wosid | 000298332200010 | - |
dc.identifier.scopusid | 2-s2.0-84255177585 | - |
dc.citation.endpage | 3318 | - |
dc.citation.number | 18 | - |
dc.citation.startpage | 3313 | - |
dc.citation.volume | 353 | - |
dc.description.isOpenAccess | N | - |
dc.contributor.affiliatedAuthor | Hong, Suck Chang | - |
dc.contributor.affiliatedAuthor | Jew, Sang-sup | - |
dc.contributor.affiliatedAuthor | Park, Hyeung-geun | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.subject.keywordPlus | AMINO-ACIDS | - |
dc.subject.keywordPlus | ASYMMETRIC-SYNTHESIS | - |
dc.subject.keywordPlus | BUTYL ESTER | - |
dc.subject.keywordPlus | STEREOSELECTIVE SYNTHESIS | - |
dc.subject.keywordPlus | NUCLEOPHILES | - |
dc.subject.keywordPlus | LACTAMS | - |
dc.subject.keywordAuthor | alpha-tert-butoxycarbonyllactams | - |
dc.subject.keywordAuthor | phase-transfer catalytic alpha-alkylation | - |
dc.subject.keywordAuthor | beta-quaternary chiral piperidines | - |
dc.subject.keywordAuthor | beta-quaternary chiral pyrrolidines | - |
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