Abstract
An effective and facile method for the synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives is described. The cyclization of 1,2-cyclopropanated sugars with olefins in the presence of BiCl3 is highly diastereoselective. 2,2-Di-substituted cyclization products were obtained in good to excellent yields.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkenes / chemistry
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Bismuth / chemistry*
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Carbohydrates / chemistry
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Chlorides / chemistry*
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Crystallography, X-Ray
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Cyclization
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Furans / chemical synthesis
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Furans / chemistry*
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Molecular Conformation
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Pyrans / chemical synthesis
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Pyrans / chemistry*
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Stereoisomerism
Substances
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Alkenes
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Carbohydrates
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Chlorides
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Furans
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Pyrans
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bismuth trichloride
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Bismuth
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furan