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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

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dc.contributor.authorHong, Suckchang-
dc.contributor.authorLee, Jihye-
dc.contributor.authorKim, Minsik-
dc.contributor.authorPark, Yohan-
dc.contributor.authorPark, Cheonhyoung-
dc.contributor.authorKim, Mi-hyun-
dc.contributor.authorJew, Sang-sup-
dc.contributor.authorPark, Hyeung-geun-
dc.date.accessioned2024-05-14T07:19:05Z-
dc.date.available2024-05-14T07:19:05Z-
dc.date.created2017-11-15-
dc.date.issued2011-04-
dc.identifier.citationJournal of the American Chemical Society, Vol.133 No.13, pp.4924-4929-
dc.identifier.issn0002-7863-
dc.identifier.urihttps://hdl.handle.net/10371/202034-
dc.description.abstractA 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.language영어-
dc.publisherAmerican Chemical Society-
dc.titleHighly enantioselective synthesis of α,α-dialkylmalonates by phase-transfer catalytic desymmetrization-
dc.title.alternativeHighly enantioselective synthesis of alpha,alpha-dialkylmalonates by phase-transfer catalytic desynnmetrization-
dc.typeArticle-
dc.identifier.doi10.1021/ja110349a-
dc.citation.journaltitleJournal of the American Chemical Society-
dc.identifier.wosid000289492700050-
dc.identifier.scopusid2-s2.0-79953870576-
dc.citation.endpage4929-
dc.citation.number13-
dc.citation.startpage4924-
dc.citation.volume133-
dc.description.isOpenAccessN-
dc.contributor.affiliatedAuthorHong, Suckchang-
dc.contributor.affiliatedAuthorJew, Sang-sup-
dc.contributor.affiliatedAuthorPark, Hyeung-geun-
dc.type.docTypeArticle-
dc.description.journalClass1-
dc.subject.keywordPlusALPHA-AMINO-ACIDS-
dc.subject.keywordPlusORGANOCATALYTIC MICHAEL ADDITION-
dc.subject.keywordPlusBETA-KETO-ESTERS-
dc.subject.keywordPlusASYMMETRIC ALKYLATION-
dc.subject.keywordPlusSTEREOSELECTIVE-SYNTHESIS-
dc.subject.keywordPlus1,3-DICARBONYL COMPOUNDS-
dc.subject.keywordPlusALLYLIC ALKYLATIONS-
dc.subject.keywordPlusCONJUGATE ADDITION-
dc.subject.keywordPlusCARBON CENTER-
dc.subject.keywordPlusNITROALKENES-
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  • College of Pharmacy
  • Department of Manufacturing Pharmacy
Research Area Development of methodologies using metal catalyst, Total synthesis of natural products

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