Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Diastereo- and Enantioselective Synthesis of Structurally Diverse Succinate, Butyrolactone, and Trifluoromethyl Derivatives by Iridium-Catalyzed Hydrogenation of Tetrasubstituted Olefins
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Show others and affiliations
Number of Authors: 62019 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 9, no 7, p. 6169-6176Article in journal (Refereed) Published
Abstract [en]

A highly efficient iridium N,P-ligand-catalyzed asymmetric hydrogenation of functionalized tetrasubstituted olefins lacking a directing group has been developed. Various structural diverse chiral succinate derivatives were obtained in high yields and excellent enantio- and diastereoselectivities (up to 99% ee) using 0.5-1.0 mol % catalyst loadings. This stereoselective reaction is applicable for the synthesis of chiral acyclic molecules (up to >99% ee) having two contiguous stereogenic centers and is compatible with various aromatic, aliphatic, and heterocyclic systems, a variety of functional groups of different electronic nature. Furthermore, this asymmetric protocol allows a short enantioselective route to the butyrolactone building block, an intermediate in the synthesis of anticancer agent BMS-871 and pharmaceuticals (2S)-(-)-Verapamil and (2S)-(-)-Gallopamil.

Place, publisher, year, edition, pages
2019. Vol. 9, no 7, p. 6169-6176
Keywords [en]
tetrasubstituted olefin, asymmetric hydrogenation, iridium catalysis, enantioselective, diastereoselective
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-171721DOI: 10.1021/acscatal.9b01508ISI: 000474812400037OAI: oai:DiVA.org:su-171721DiVA, id: diva2:1350411
Available from: 2019-09-11 Created: 2019-09-11 Last updated: 2019-09-11Bibliographically approved

Open Access in DiVA

No full text in DiVA

Other links

Publisher's full text

Search in DiVA

By author/editor
Ponra, SudiptaYang, JianpingWu, HaiboEriksson, LarsAndersson, Pher G.
By organisation
Department of Organic ChemistryDepartment of Materials and Environmental Chemistry (MMK)
In the same journal
ACS Catalysis
Chemical Sciences

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 1 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf