Dirhodium carboxylate catalysts from 2-fenchyloxy or 2-menthyloxy arylacetic acids: enantioselective C-H insertion, aromatic addition and oxonium ylide formation/rearrangement

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dc.contributor.authorBuckley, Aoife
dc.contributor.authorCrowley, Daniel C.
dc.contributor.authorBrouder, Thomas A.
dc.contributor.authorFord, Alan
dc.contributor.authorKhandavilli, Udaya Bhaskara Rao
dc.contributor.authorLawrence, Simon E.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderIrish Research Councilen
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderEuropean Regional Development Funden
dc.date.accessioned2022-02-25T11:45:32Z
dc.date.available2022-02-25T11:45:32Z
dc.date.issued2021-10
dc.date.updated2022-02-24T16:46:13Z
dc.description.abstractA new class of dirhodium carboxylate catalysts have been designed and synthesized from 2-fenchyloxy or 2-menthyloxy arylacetic acids which display excellent enantioselectivity across a range of transformations of alpha-diazocarbonyl compounds. The catalysts were successfully applied to enantioselective C-H insertion reactions of aryldiazoacetates and alpha-diazo-beta-oxosulfones affording the respective products in up to 93 % ee with excellent trans diastereoselectivity in most cases. Furthermore, efficient desymmetrization in an intramolecular C-H insertion was achieved. In addition, these catalysts prove highly enantioselective for intramolecular aromatic addition with up to 88% ee, and oxonium ylide formation and rearrangement with up to 74% ee.en
dc.description.sponsorshipIrish Research Council (AMB [GOIPG/2013/225] DC [GOIPG/2015/2872], TAB [GOIPG/2015/3188]); Science Foundation Ireland (SSPC3 Pharm5 12/RC/2275_2)en
dc.description.statusPeer revieweden
dc.description.versionPublished Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationBuckley, A. M., Crowley D. C., Brouder; T. A., Ford, A; Khandavilli, U. B. R., Lawrence, S. E. and Maguire, A. R. (2021) 'Dirhodium carboxylate catalysts from 2-fenchyloxy or 2-menthyloxy arylacetic acids: enantioselective C-H insertion, aromatic addition and oxonium ylide formation/rearrangement', ChemCatChem, 13 , pp. 4318-4324. doi:10.1002/cctc.202100924en
dc.identifier.doi10.1002/cctc.202100924en
dc.identifier.endpage4324en
dc.identifier.issn1867-3880
dc.identifier.journaltitleChemCatChemen
dc.identifier.startpage4318en
dc.identifier.urihttps://hdl.handle.net/10468/12603
dc.identifier.volume13en
dc.language.isoenen
dc.publisherWILEY-VCH Verlagen
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/en
dc.rights© 2021, the Authors. ChemCatChem published by Wiley-VCHGmbH. This is an open access article under the terms of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).en
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/en
dc.subjectIntramolecular buchner reactionen
dc.subjectSigmatropic rearrangementen
dc.subjectAsymmetric-synthesisen
dc.subjectCarbene insertionen
dc.subjectHIV-1 integraseen
dc.subjectComplexesen
dc.subjectBonden
dc.subjectFunctionalizationen
dc.subjectDiazoketonesen
dc.subjectDerivativesen
dc.titleDirhodium carboxylate catalysts from 2-fenchyloxy or 2-menthyloxy arylacetic acids: enantioselective C-H insertion, aromatic addition and oxonium ylide formation/rearrangementen
dc.typeArticle (peer-reviewed)en
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