Indium trichloride catalyzed Ferrier rearrangement – Facile synthesis of 2,3-unsaturated glycosides
نویسندگان
چکیده
منابع مشابه
Cyanuric Chloride as an Efficient Catalyst for the Synthesis of 2,3-Unsaturated O-Glycosides by Ferrier Rearrangement
Cyanuric chloride has been found to be an efficient catalyst for the synthesis of 2,3-unsaturated O-glycosides from the reaction of 3,4,6-tri-O-acetyl-D-glucal and a wide range of alcohols in dichloromethane at room temperature. The experimental procedure is simple, and the products are obtained in high yields.
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A mild and highly efficient stereoselective reaction of 3,4,6-tri-O-acetyl-Dglucal with a variety of nucleophiles, viz. alcohols, phenols, thiols, thiophenols, and allyl trimethyl silane (TMS), in the presence of 5 mol% of lanthanum(III) nitrate hexahydrate under solvent-free conditions yielded the corresponding 2,3-unsaturated glycopyranosides (pseudoglycals) in excellent yields.
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A versatile and high-yielding indium trichloride mediated cyclization reaction of silylated homoallylic alcohols, thiols, or amines with aldehydes or epoxides is described as a rapid route to a range of unsaturated heterocycles. The excellent diastereoselectivity observed offers a method of wide scope and generality.
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A highly efficient and general method for the synthesis of aryloylamido coumarinsderivatives by a three-component condensation of 4-hydroxycoumarin or 4-hydroxy-6-methylpyran-1-one, aryl glyoxals and benzamide in the presence of nano silica supported tin(II) chloride as a heterogeneous catalyst is established. In this method, SnCl2/nano SiO2 wasused as green and reusable catalyst. Excellent yie...
متن کاملDirect coupling of alcohols with alkenylsilanes catalyzed by indium trichloride or bismuth tribromide.
Indium halides or bismuth halides catalyzed the coupling of various alcohols with alkenylsilanes to give the corresponding alkenes stereospecifically without any other activators.
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ژورنال
عنوان ژورنال: Arkivoc
سال: 2005
ISSN: 1551-7012
DOI: 10.3998/ark.5550190.0005.811