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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
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 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.