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  • Naidu, Veluru RameshKTH,Organisk kemi (author)

Direct Organocatalytic Oxo-Metathesis, a trans-Selective Carbocation-Catalyzed Olefination of Aldehydes

  • Article/chapterEnglish2015

Publisher, publication year, extent ...

  • 2015-02-05
  • Wiley,2015
  • printrdacarrier

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  • LIBRIS-ID:oai:DiVA.org:kth-164466
  • https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-164466URI
  • https://doi.org/10.1002/ejoc.201403651DOI

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  • Language:English
  • Summary in:English

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

Notes

  • QC 20150422
  • A direct organocatalytic carbonyl/olefin oxo-metathesis has been developed. The reaction is catalyzed by trityl tetrafluoroborate (TrBF4) and utilizes unactivated alkenes for the olefination of aromatic aldehydes to give trans -alkylstyrenes in yields of 44-85% with only acetone as the byproduct. The pronounced Lewis acidity of the carbocation results in unusual reactivity that is proposed to catalyze a stepwise [2+2] cycloaddition to give an oxetane intermediate. Fragmentation of the latter in a formal retro [2+2] reaction gives the oxo-metathesis product.

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  • Bah, JuhoKTH,Organisk kemi(Swepub:kth)u1gpvftb (author)
  • Franzén, JohanKTH,Organisk kemi(Swepub:kth)u1991vf3 (author)
  • KTHOrganisk kemi (creator_code:org_t)

Related titles

  • In:European Journal of Organic Chemistry: Wiley:8, s. 1834-18391434-193X1099-0690

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Naidu, Veluru Ra ...
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NATURAL SCIENCES
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European Journal ...
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Royal Institute of Technology

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