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Highly enantioselective synthesis of α,α-dialkylmalonates by phase-transfer catalytic desymmetrization : Highly enantioselective synthesis of alpha,alpha-dialkylmalonates by phase-transfer catalytic desynnmetrization
DC Field | Value | Language |
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dc.contributor.author | Hong, Suckchang | - |
dc.contributor.author | Lee, Jihye | - |
dc.contributor.author | Kim, Minsik | - |
dc.contributor.author | Park, Yohan | - |
dc.contributor.author | Park, Cheonhyoung | - |
dc.contributor.author | Kim, Mi-hyun | - |
dc.contributor.author | Jew, Sang-sup | - |
dc.contributor.author | Park, Hyeung-geun | - |
dc.date.accessioned | 2024-05-14T07:19:05Z | - |
dc.date.available | 2024-05-14T07:19:05Z | - |
dc.date.created | 2017-11-15 | - |
dc.date.issued | 2011-04 | - |
dc.identifier.citation | Journal of the American Chemical Society, Vol.133 No.13, pp.4924-4929 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | https://hdl.handle.net/10371/202034 | - |
dc.description.abstract | A novel enantioselective synthetic method for the construction of a quaternary carbon center from malonates via phase-transfer catalytic (PTC) alkylation has been developed. The asymmetric alpha-alkylation of diphenylmethyl tertbutyl alpha-alkylmalonates with alkylating agents under phase-transfer catalysis conditions (aq 50% KOH, toluene, 0 degrees C) in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide (8) as PTC catalyst afforded the corresponding alpha,alpha-dialkylmalonates in high chemical (up to 99%) and optical yields (up to 97% ee) which could be readily converted to versatile chiral intermediates. Notably, the direct double alpha-alkylations of diphenylmethyl tert-butyl malonate also provided the corresponding alpha,alpha-dialkylmalonates without loss of enantioselectivity. The synthetic potential of this method has been demonstrated by the preparation of alpha,alpha-dialkylamino acid and oxindole systems. | - |
dc.language | 영어 | - |
dc.publisher | American Chemical Society | - |
dc.title | Highly enantioselective synthesis of α,α-dialkylmalonates by phase-transfer catalytic desymmetrization | - |
dc.title.alternative | Highly enantioselective synthesis of alpha,alpha-dialkylmalonates by phase-transfer catalytic desynnmetrization | - |
dc.type | Article | - |
dc.identifier.doi | 10.1021/ja110349a | - |
dc.citation.journaltitle | Journal of the American Chemical Society | - |
dc.identifier.wosid | 000289492700050 | - |
dc.identifier.scopusid | 2-s2.0-79953870576 | - |
dc.citation.endpage | 4929 | - |
dc.citation.number | 13 | - |
dc.citation.startpage | 4924 | - |
dc.citation.volume | 133 | - |
dc.description.isOpenAccess | N | - |
dc.contributor.affiliatedAuthor | Hong, Suckchang | - |
dc.contributor.affiliatedAuthor | Jew, Sang-sup | - |
dc.contributor.affiliatedAuthor | Park, Hyeung-geun | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.subject.keywordPlus | ALPHA-AMINO-ACIDS | - |
dc.subject.keywordPlus | ORGANOCATALYTIC MICHAEL ADDITION | - |
dc.subject.keywordPlus | BETA-KETO-ESTERS | - |
dc.subject.keywordPlus | ASYMMETRIC ALKYLATION | - |
dc.subject.keywordPlus | STEREOSELECTIVE-SYNTHESIS | - |
dc.subject.keywordPlus | 1,3-DICARBONYL COMPOUNDS | - |
dc.subject.keywordPlus | ALLYLIC ALKYLATIONS | - |
dc.subject.keywordPlus | CONJUGATE ADDITION | - |
dc.subject.keywordPlus | CARBON CENTER | - |
dc.subject.keywordPlus | NITROALKENES | - |
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