Chemistry : A European Journal [ECMC, SOCAT, LCSOM]

Abstract :

A new way of introducing a N-heterocyclic carbene cap onto cyclodextrins has been devised. The benzimidazolium intermediates were found to behave as receptors towards cavity matching anions. The corresponding C1- and C2-symmetrical regioisomeric carbene gold(I) complexes have been tested in a benchmark asymmetric cycloisomerization of 1,6-enynes. Up to 50% ee was achieved for the enantioselective cycloisomerization of N-allyl-4-methyl-N-(3-phenylprop-2-yn-1-yl)benzenesulfonamide.

Reference :

Zeyneb Kaya, Lucile Andna, Dominique Matt, Embarek Bentouhami, Jean‐Pierre Djukic and Dominique Armspach

Benzimidazolium-and Benzimidazolilydene-Capped Cyclodextrins: NewPerspectives in Anion Encapsulation and Gold-Catalyzed Cycloisomerization of 1,6-Enynes

Chem. Eur. J. 2018, 24 17921-17926 - DOI: 10.1002/chem.201804710

Contact chercheur :

Dominique Armspach, ECMC, Institut de Chimie (UMR 7177).