Endre søk
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
Intramolecular substitutions of secondary and tertiary alcohols with chirality transfer by an iron(III) catalyst
Vise andre og tillknytning
2019 (engelsk)Inngår i: Nature Communications, E-ISSN 2041-1723, Vol. 10, nr 1, artikkel-id 3826Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Optically pure alcohols are abundant in nature and attractive as feedstock for organic synthesis but challenging for further transformation using atom efficient and sustainable methodologies, particularly when there is a desire to conserve the chirality. Usually, substitution of the OH group of stereogenic alcohols with conservation of chirality requires derivatization as part of a complex, stoichiometric procedure. We herein demonstrate that a simple, inexpensive, and environmentally benign iron(III) catalyst promotes the direct intramolecular substitution of enantiomerically enriched secondary and tertiary alcohols with O-, N-, and S-centered nucleophiles to generate valuable 5-membered, 6-membered and aryl-fused 6-membered heterocyclic compounds with chirality transfer and water as the only byproduct. The power of the methodology is demonstrated in the total synthesis of (+)-lentiginosine from D-glucose where iron-catalysis is used in a key step. Adoption of this methodology will contribute towards the transition to sustainable and bio-based processes in the pharmaceutical and agrochemical industries. © 2019, The Author(s).

sted, utgiver, år, opplag, sider
Nature Publishing Group , 2019. Vol. 10, nr 1, artikkel-id 3826
Emneord [en]
alcohol, benzyl alcohol, ferric ion, heterocyclic compound, Lewis acid, nucleophile, secondary alcohol, teritiary alcohol, unclassified drug, catalyst, drug, iron, methodology, pharmaceutical industry, transformation, Article, chemical reaction kinetics, chirality, column chromatography, drug industry, electrophysiology, enzyme kinetics, intramolecular substitution, isotope labeling, screening, stoichiometry, substitution reaction
HSV kategori
Identifikatorer
URN: urn:nbn:se:ri:diva-57304DOI: 10.1038/s41467-019-11838-xScopus ID: 2-s2.0-85071045613OAI: oai:DiVA.org:ri-57304DiVA, id: diva2:1616704
Merknad

 Funding details: Svenska Forskningsrådet Formas; Funding details: Stiftelsen Olle Engkvist Byggmästare; Funding details: Vetenskapsrådet, VR; Funding text 1: J.S.M.S. thanks the Swedish Research Council, FORMAS and Stiftelsen Olle Engkvist Byggmastare for financial support. The simulations were performed on resources provided by the Swedish National Infrastructure for Computing (SNIC) at UPPMAX and NSC. We are grateful to Prof. F. Himo for advising us with the DFT calculations.

Tilgjengelig fra: 2021-12-03 Laget: 2021-12-03 Sist oppdatert: 2023-03-28bibliografisk kontrollert

Open Access i DiVA

Fulltekst mangler i DiVA

Andre lenker

Forlagets fulltekstScopus

Person

Ayub, Rabia

Søk i DiVA

Av forfatter/redaktør
Ayub, Rabia
I samme tidsskrift
Nature Communications

Søk utenfor DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric

doi
urn-nbn
Totalt: 4 treff
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
v. 2.43.0