Synthesis of Six-Membered N-Heterocyclic Carbene Precursors Based on Camphor

Jan Šegina; Luka Ciber; Helena Brodnik; Franc Požgan; Jurij Svete; Bogdan Štefane; Uroš Grošelj

doi:10.20944/preprints202311.1020.v1

A peer-reviewed article of this Preprint also exists.

Šegina, J.; Ciber, L.; Brodnik, H.; Požgan, F.; Svete, J.; Štefane, B.; Grošelj, U. Synthesis of Six-Membered N-Heterocyclic Carbene Precursors Based on Camphor. Molecules 2023, 28, 7973. Šegina, J.; Ciber, L.; Brodnik, H.; Požgan, F.; Svete, J.; Štefane, B.; Grošelj, U. Synthesis of Six-Membered N-Heterocyclic Carbene Precursors Based on Camphor. Molecules 2023, 28, 7973.

Abstract

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 N-heterocyclic carbene precursors were investigated in an asymmetric benzoin reaction. All new compounds were fully characterized and the absolute configurations were determined by X-ray diffraction and NOESY measurements.

Keywords

ketopinic acid; amidation, reduction, diamines; N-heterocyclic carbene precursors; asymmetric catalysis; amidinium salts; hydrolysis

Subject

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Synthesis of Six-Membered N-Heterocyclic Carbene Precursors Based on Camphor

Abstract

Keywords

Subject

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