Benzimidazolium‐ and Benzimidazolilydene‐Capped Cyclodextrins: New Perspectives in Anion Encapsulation and Gold‐Catalyzed Cycloisomerization of 1,6‐Enynes | Zendy

Kaya Zeyneb | Zendy; Andna Lucile | Zendy; Matt Dominique | Zendy; Bentouhami Embarek | Zendy; Djukic JeanPierre | Zendy; Armspach Dominique | Zendy

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Benzimidazolium‐ and Benzimidazolilydene‐Capped Cyclodextrins: New Perspectives in Anion Encapsulation and Gold‐Catalyzed Cycloisomerization of 1,6‐Enynes

Author(s) -

Kaya Zeyneb,

Andna Lucile,

Matt Dominique,

Bentouhami Embarek,

Djukic JeanPierre,

Armspach Dominique

Publication year - 2018

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201804710

Subject(s) - cycloisomerization , carbene , enantioselective synthesis , chemistry , catalysis , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry

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 C 1 ‐ and C 2 ‐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.

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