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  • Bunrit, AnonUppsala universitet,Institutionen för kemi - BMC (author)

Brønsted Acid-Catalyzed Intramolecular Nucleophilic Substitution of the Hydroxyl Group in Stereogenic Alcohols with Chirality Transfer

  • Article/chapterEnglish2015

Publisher, publication year, extent ...

  • 2015-04-01
  • American Chemical Society (ACS),2015
  • printrdacarrier

Numbers

  • LIBRIS-ID:oai:DiVA.org:su-117729
  • https://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-117729URI
  • https://doi.org/10.1021/jacs.5b02013DOI
  • https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-253254URI

Supplementary language notes

  • Language:English
  • Summary in:English

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  • Subject category:ref swepub-contenttype
  • Subject category:art swepub-publicationtype

Notes

  • The hydroxyl group of enantioenriched benzyl, propargyl, allyl, and alkyl alcohols has been intramolecularly displaced by uncharged O-, N-, and S-centered nucleophiles to yield enantioenriched tetrahydrofuran, pyrrolidine, and tetrahydrothiophene derivatives with phosphinic acid catalysis. The five-membered heterocyclic products are generated in good to excellent yields, with high degree of chirality transfer, and water as the only side-product. Racemization experiments show that phosphinic acid does not promote S(N)1 reactivity. Density functional theory calculations corroborate a reaction pathway where the phosphinic acid operates as a bifunctional catalyst in the intramolecular substitution reaction. In this mechanism, the acidic proton of the phosphinic acid protonates the hydroxyl group, enhancing the leaving group ability. Simultaneously, the oxo group of phosphinic acid operates as a base abstracting the nucleophilic proton and thus enhancing the nucleophilicity. This reaction will open up new atom efficient techniques that enable alcohols to be used as nucleofuges in substitution reactions in the future.

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  • Dahlstrand, ChristianUppsala universitet,Institutionen för kemi - BMC(Swepub:uu)chrda875 (author)
  • Olsson, Sandra K.Uppsala universitet,Institutionen för kemi - BMC(Swepub:uu)sanol809 (author)
  • Srifa, PemikarUppsala universitet,Institutionen för kemi - BMC(Swepub:uu)pemsr463 (author)
  • Huang, GenpingStockholms universitet,Institutionen för organisk kemi(Swepub:su)ghuan (author)
  • Orthaber, AndreasUppsala universitet,Molekylär biomimetik(Swepub:uu)ortan368 (author)
  • Sjöberg, Per J. R.Uppsala universitet,Analytisk kemi(Swepub:uu)psj18455 (author)
  • Biswas, SrijitUppsala universitet,Institutionen för kemi - BMC(Swepub:uu)sribi464 (author)
  • Himo, FahmiStockholms universitet,Institutionen för organisk kemi(Swepub:su)himo (author)
  • Samec, Joseph S. M.Uppsala universitet,Institutionen för kemi - BMC(Swepub:uu)jossa512 (author)
  • Uppsala universitetInstitutionen för kemi - BMC (creator_code:org_t)

Related titles

  • In:Journal of the American Chemical Society: American Chemical Society (ACS)137:14, s. 4646-46490002-78631520-5126

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