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

Author:

Šegina Jan1,Ciber Luka1,Brodnik Helena1,Požgan Franc1ORCID,Svete Jurij1ORCID,Štefane Bogdan1ORCID,Grošelj Uroš1ORCID

Affiliation:

1. Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna Pot 113, 1000 Ljubljana, Slovenia

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 via X-ray diffraction and NOESY measurements.

Funder

Slovenian Research Agency

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

Reference43 articles.

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5. Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes;Kitamura;J. Am. Chem. Soc.,1986

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