Direct Ferrier rearrangement on unactivated glycals catalyzed by indium(III) chloride

Tetrahedron Letters

Volumn 50, Issue 27, 2009, Pages 3970-3973

  Nagaraj, Paramathevar ^a   Ramesh, Namakkal G ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY DELHI   (India)

Author keywords

Disaccharides; Ferrier rearrangement; Glycals; Glycosylation; Indium(III) chloride; Lewis acid

Indexed keywords

ALCOHOL; GLUCONATE CALCIUM; GLYCOSIDE; HYDROXYL GROUP; INDIUM CHLORIDE; NUCLEOPHILE; PHENOL;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENVIRONMENTAL TEMPERATURE; METHODOLOGY; REACTION ANALYSIS;

EID: 65549132804     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.084     Document Type: Article

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79. 3 was added and the reaction mixture was stirred under argon atmosphere for specific time mentioned in Tables 1 and 2. The reaction mixture was then quenched with water and extracted with chloroform (3 × 50 mL). The combined organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated. The product was purified by column chromatography with hexane/ethyl acetate as an eluent to obtain the corresponding 2,3-unsaturated glycosides (4-8, 10-18).