A Comparative Study of Confining Ligands Derived from Methylated Cyclodextrins in Gold‐Catalyzed Cycloisomerization of 1, 6‐Enynes. Issue 28 (12th July 2019)

• Record Type: Journal Article
• Authors: Kaya, Zeyneb; Andna, Lucile; Matt, Dominique; Bentouhami, Embarek; Djukic, Jean‐Pierre; Armspach, Dominique
• Is Part Of: European journal of organic chemistry. Issue 28(2019)
• Page Start: 4528
• Page End: 4537
• Publication Date: 2019-07-12
• Subjects: Cyclodextrins -- Gold -- Cycloisomerization -- Phosphorus -- NHC; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900631
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Gold(I) complexes containing monodentate P III ‐ligands built upon methylated α‐cyclodextrins have been synthesized and assessed in the cycloisomerization of 1, 6‐enynes, two of the reactions studied involving prochiral substrates. Their performance was compared with that of previously reported mononuclear and dinuclear α‐ and β‐cyclodextrin‐based Au I complexes. Enantiodiscrimination was found to be strongly dependent on the ability of the ligand to position metal‐coordinated substrates inside the cyclodextrin core. Abstract : α‐ and β‐cyclodextrin derivatives equipped with one or two P III ‐containing handles behave as enantiodiscriminating ligands in the gold‐catalyzed cycloisomerization of prochiral N‐tethered 1, 6‐enynes. Enantioselectivity was found to be dependent on the ability of the ligand to position the metal‐coordinated substrate inside the cavity.