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- Martinez-Erro, SamuelStockholms universitet,Institutionen för organisk kemi (author)
Base-Catalyzed Stereospecific Isomerization of Electron-Deficient Allylic Alcohols and Ethers through Ion-Pairing
- Article/chapterEnglish2016
Publisher, publication year, extent ...
- 2016-09-30
- American Chemical Society (ACS),2016
- printrdacarrier
Numbers
- LIBRIS-ID:oai:DiVA.org:kth-195245
- https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-195245URI
- https://doi.org/10.1021/jacs.6b08350DOI
- https://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-136066URI
Supplementary language notes
- Language:English
- Summary in:English
Part of subdatabase
- SwePubSwePub
Classification
Notes
- QC 20161116
- A mild base-catalyzed strategy for the isomerization of allylic alcohols and allylic ethers has been developed. Experimental and computational investigations indicate that transition metal catalysts are not required when basic additives are present. As in the case of using transition metals under basic conditions, the isomerization catalyzed solely by base also follows a stereospecific pathway. The reaction is initiated by a rate-limiting deprotonation. Formation of an intimate ion pair between an allylic anion and the conjugate acid of the base results in efficient transfer of chirality. Through this mechanism, stereochemical information contained in the allylic alcohols is transferred to the ketone products. The stereospecific isomerization is also applicable for the first time to allylic ethers, yielding synthetically valuable enantioenriched (up to 97% ee) enol ethers.
Subject headings and genre
- NATURVETENSKAP Kemi hsv//swe
- NATURAL SCIENCES Chemical Sciences hsv//eng
- NATURVETENSKAP Kemi Organisk kemi hsv//swe
- NATURAL SCIENCES Chemical Sciences Organic Chemistry hsv//eng
- Catalysis
- Catalysts
- Ions
- Isomerization
- Isomers
- Ketones
- Transition metals
- Allylic alcohol
- Allylic ethers
- Base catalyzed
- Basic conditions
- Computational investigation
- Conjugate acid
- Electron-deficient
- Transition metal catalysts
- Ethers
- organisk kemi
Added entries (persons, corporate bodies, meetings, titles ...)
- Sanz-Marco, AmparoStockholms universitet,Institutionen för organisk kemi(Swepub:su)asanz (author)
- Bermejo Gómez, AntonioStockholms universitet,Institutionen för organisk kemi(Swepub:su)antbe (author)
- Vazquez-Romero, AnaStockholms universitet,Institutionen för organisk kemi(Swepub:su)avz (author)
- Ahlquist, Mårten S. G.KTH,Teoretisk kemi och biologi(Swepub:kth)u1agoeae (author)
- Martín-Matute, BelénStockholms universitet,Institutionen för organisk kemi(Swepub:su)bemar (author)
- Stockholms universitetInstitutionen för organisk kemi (creator_code:org_t)
Related titles
- In:Journal of the American Chemical Society: American Chemical Society (ACS)138:40, s. 13408-134140002-78631520-5126
Internet link
- https://doi.org/10.1021/jacs.6b08350
- https://doi.org/10.1021/jacs.6b08350Fulltext
- https://su.diva-portal.org/smash/get/diva2:1057281/FULLTEXT01.pdffulltext:print
- https://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-195245
- https://doi.org/10.1021/jacs.6b08350
- https://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-136066
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