6283-72-3Relevant articles and documents
Enantiselective Lactonization of Sodium 4-Hydroxypimelate under Abiological Conditions
Fuji, Kaoru,Node, Manabu,Terada, Shunji,Murata, Makoto,Nagasawa, Hideko
, p. 6404 - 6406 (1985)
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Radical addition of 2-iodoalkanamide or 2-iodoalkanoic acid to alkenes with a water-soluble radical initiator in aqueous media: Facile synthesis of γ-lactones
Yorimitsu,Wakabayashi,Shinokubo,Oshima
, p. 1963 - 1970 (2007/10/03)
Radical reactions in water or aqueous ethanol using a water-soluble radical initiator are described. Heating a mixture of 2-iodoacetamide and 5-hexen-1-ol in water at 75 °C in the presence of a water-soluble radical initiator, 4,4′-azobis 4-cyanopentanoic acid), afforded 5-(4-hydroxybutyl)dihydrofuran-2(3H)-one in 95% yield. The use of 2-iodoacetic acid in place of 2-iodoacetamide also gave the same γ-lactone in 93% yield. The reaction of 2-iodoacetamide with 1-octene in aqueous ethanol was initiated by 2,2′-azobis(2-methylpropanamidine) dihydrochloride to provide γ-decanolactone. Employing water as a solvent is crucial to obtain lactone in satisfactory yield.
Titanocene-Catalyzed Reduction of Lactones to Lactols
Verdaguer, Xavier,Hansen, Marcus C.,Berk, Scott C.,Buchwald, Stephen L.
, p. 8522 - 8528 (2007/10/03)
A convenient method for the conversion of lactones to lactols is described. The hydrosilylation to lactols is carried out via air-stable titanocene difluoride or a titanocene diphenoxide precatalyst using inexpensive polymethylhydrosiloxane (PMHS) as the stoichiometric reductant. These procedures have been demonstrated with a variety of substrates and proceed in good to excellent yield.