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Pregled bibliografske jedinice broj: 780765

Mild and Chemoselective Lactone Ring-Opening with (TMS)ONa. Mechanistic Studies and Application to Sweroside Derivatives

Lemoine, H.; Markovic, D.; Deguin, B.
Mild and Chemoselective Lactone Ring-Opening with (TMS)ONa. Mechanistic Studies and Application to Sweroside Derivatives // Journal of organic chemistry, 79 (2014), 4358-4366 doi:10.1021/jo500220h (međunarodna recenzija, članak, znanstveni)

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Naslov
Mild and Chemoselective Lactone Ring-Opening with (TMS)ONa. Mechanistic Studies and Application to Sweroside Derivatives

Autori
Lemoine, H. ; Markovic, D. ; Deguin, B.

Izvornik
Journal of organic chemistry (0022-3263) 79 (2014); 4358-4366

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Lactones (TMS)ONa; Mechanistic Studies; Sweroside;

Sažetak
Mild and chemoselective opening of lactones with sodium trimethylsilanolate in high yields and aprotic solvents is described. Kinetic studies demonstrate that the B(Ac)2 mechanistic pathway is followed. Nucleophilic attack of silanolate onto the carbonyl of the lactone moiety is the rate-determining step. NaOH present as an impurity accelerates the reaction. The method was further applied to the base-sensitive and stable lactones derived from highly functionalized iridoid derivatives.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA

Profili:

Avatar Url Dean Marković (autor)

Poveznice na cjeloviti tekst rada:

doi pubs.acs.org

Citiraj ovu publikaciju:

Lemoine, H.; Markovic, D.; Deguin, B.
Mild and Chemoselective Lactone Ring-Opening with (TMS)ONa. Mechanistic Studies and Application to Sweroside Derivatives // Journal of organic chemistry, 79 (2014), 4358-4366 doi:10.1021/jo500220h (međunarodna recenzija, članak, znanstveni)
Lemoine, H., Markovic, D. & Deguin, B. (2014) Mild and Chemoselective Lactone Ring-Opening with (TMS)ONa. Mechanistic Studies and Application to Sweroside Derivatives. Journal of organic chemistry, 79, 4358-4366 doi:10.1021/jo500220h.
@article{article, author = {Lemoine, H. and Markovic, D. and Deguin, B.}, year = {2014}, pages = {4358-4366}, DOI = {10.1021/jo500220h}, keywords = {Lactones (TMS)ONa, Mechanistic Studies, Sweroside, }, journal = {Journal of organic chemistry}, doi = {10.1021/jo500220h}, volume = {79}, issn = {0022-3263}, title = {Mild and Chemoselective Lactone Ring-Opening with (TMS)ONa. Mechanistic Studies and Application to Sweroside Derivatives}, keyword = {Lactones (TMS)ONa, Mechanistic Studies, Sweroside, } }
@article{article, author = {Lemoine, H. and Markovic, D. and Deguin, B.}, year = {2014}, pages = {4358-4366}, DOI = {10.1021/jo500220h}, keywords = {Lactones (TMS)ONa, Mechanistic Studies, Sweroside, }, journal = {Journal of organic chemistry}, doi = {10.1021/jo500220h}, volume = {79}, issn = {0022-3263}, title = {Mild and Chemoselective Lactone Ring-Opening with (TMS)ONa. Mechanistic Studies and Application to Sweroside Derivatives}, keyword = {Lactones (TMS)ONa, Mechanistic Studies, Sweroside, } }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE

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