Synthesis of six-membered N-heterocyclic carbene precursors based on camphor

Šegina, Jan (author), Ciber, Luka (author), Brodnik Žugelj, Helena (author), Požgan, Franc (author), Svete, Jurij (author), Štefane, Bogdan (author), Grošelj, Uroš (author)

The endo- and exo-N-heterocyclic carbene precursors based on camphor were prepared diastereoselectively in five synthetic steps starting from (1S)-(+)-ketopinic acid. The obtained Nheterocyclic carbene precursors were investigated in an asymmetric benzoin reaction. All newcompounds were fully characterized, and the absolute configurations were determined via X-ray diffraction and NOESY measurements.

• Language: English
• Keywords: ketopinic acid, amidation, reduction, diamines, N-heterocyclic carbene precursors, asymmetric catalysis, amidinium salts, hydrolysis
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Publication date: 01.12.2023
• Year: 2023
• Number of pages: 12 str.
• Numbering: Vol. 28, iss. 24, art. 7973
• PID: 20.500.12556/RUL-152885
• UDC: 547.8.057
• ISSN on article: 1420-3049
• DOI: 10.3390/molecules28247973
• COBISS.SI-ID: 176421635
• Publication date in RUL: 11.12.2023

Record is a part of a journal

• Title: Molecules
• Shortened title: Molecules
• Publisher: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

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: ketopinska kislina, amidiranje, redukcija, diamini, N-heterociklični prekurzorji karbena, asimetrična kataliza, amidinijeve soli, hidroliza

Projects

• Funder: ARRS - Slovenian Research Agency
• Project number: P1-0179
• Name: Napredna organska sinteza in kataliza