Gold-catalyzed intramolecular hydroalkoxylation/cyclization of conjugated dienyl alcohols

Catalytic intramolecular additions of hydroxyl groups to tethered conjugated dienes are described. The reactions proceed smoothly at 60°C in the presence of 5mol% of (PPh3)AuCl/AgOTf as a catalyst. A broad range of structurally diverse conjugated dienes produce substituted tetrahydrofurans and tetra...

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Veröffentlicht in:	Tetrahedron 2012-06, Vol.68 (24), p.4805-4812
Hauptverfasser:	Chandrasekhar, B., Ryu, Jae-Sang
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohol Catalysis Catalysts Catalysts: preparations and properties Chemistry Conjugated diene Construction Cyclization Dienes Ethers Exact sciences and technology General and physical chemistry Gold Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Hydroalkoxylation Hydroxyl groups Organic chemistry Organometalloidal and organometallic compounds P derivatives Preparations and properties Tetrahedrons Tetrahydrofuran Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Beschreibung
Zusammenfassung:	Catalytic intramolecular additions of hydroxyl groups to tethered conjugated dienes are described. The reactions proceed smoothly at 60°C in the presence of 5mol% of (PPh3)AuCl/AgOTf as a catalyst. A broad range of structurally diverse conjugated dienes produce substituted tetrahydrofurans and tetrahydropyrans in good yields. This reaction represents an atom-economic route to construct five- and six-membered cyclic ethers. [Display omitted]
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2012.03.120