Catalytic performance of Noyori–Ikariya-type ruthenium complex with tethered syn-ULTAM ligand for the asymmetric transfer hydrogenation of ketones

Hašanová, Simona (author), Cingl, Jernej (author), Tomašič, Tihomir (author), Cotman, Andrej Emanuel (author)

The ruthenium complex of the tethered syn-ULTAM ligand, i.e. syn-3-(α-aminobenzyl)-benzo-γ-sultam, has been evaluated for the asymmetric transfer hydrogenation (ATH) of a variety of ketones in formic acid/triethylamine mixture. Its performance was similar to the established Noyori–Ikariya-type catalysts for the reduction of benzo-fused cyclic ketones, but the enantioselectivity for the reduction of acetophenone was only moderate. The syn-ULTAM-based catalyst was particularly efficient and enantioselective for ATH of the sterically demanding α,α-disubstituted ketones. Moreover, we report a divergent ATH of 2-phenyl-1,3-indandione to either cis-2-phenyl-1-indanol, or cis,trans-2-phenyl-1,3-indandiol.

• Language: English
• Keywords: asymmetric synthesis, ruthenium, hydrogenation, alcohol
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FFA - Faculty of Pharmacy
• Publication status: Published
• Publication version: Version of Record
• Year: 2024
• Number of pages: 4 str.
• Numbering: Vol. 138, art. 154984
• PID: 20.500.12556/RUL-154836
• UDC: 66.094.1
• ISSN on article: 0040-4039
• DOI: 10.1016/j.tetlet.2024.154984
• COBISS.SI-ID: 187162371
• Publication date in RUL: 05.03.2024

Record is a part of a journal

• Title: Tetrahedron letters
• Shortened title: Tetrahedron lett.
• Publisher: Elsevier
• ISSN: 0040-4039
• COBISS.SI-ID: 972815

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: asimetrična sinteza, rutenij, hidrogenacija, hidrogeniranje, alkohol

Projects

• Funder: ARIS - Slovenian Research and Innovation Agency
• Project number: P1-0208
• Name: Farmacevtska kemija: načrtovanje, sinteza in vrednotenje učinkovin

• Funder: ARIS - Slovenian Research and Innovation Agency
• Project number: J1-50023
• Name: 3DfluorCO - tridimenzionalni fluor vsebujoči bioizosteri karbonila: asimetrična sinteza in validacija