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Direct Organocataly...
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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 ...
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2015-02-05
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Wiley,2015
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printrdacarrier
Numbers
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LIBRIS-ID:oai:DiVA.org:kth-164466
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https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-164466URI
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https://doi.org/10.1002/ejoc.201403651DOI
Supplementary language notes
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Language:English
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Summary in:English
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Subject category:ref swepub-contenttype
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Subject category:art swepub-publicationtype
Notes
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QC 20150422
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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)
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Franzén, JohanKTH,Organisk kemi(Swepub:kth)u1991vf3
(author)
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KTHOrganisk kemi
(creator_code:org_t)
Related titles
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In:European Journal of Organic Chemistry: Wiley:8, s. 1834-18391434-193X1099-0690
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