Abstract
A new and convenient synthesis of benzo-fused 8-oxabicyclo[3.2.1]octane and 9-oxabicyclo[4.2.1]nonane derivatives are described. The reaction involved a TiCl(4)-mediated tandem carbonyl or imine addition followed by a Friedel-Crafts cyclization to provide these functionalized derivatives in good to excellent yields and high diastereoselectivity.
© 2012 American Chemical Society
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Alkanes / chemical synthesis*
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Alkanes / chemistry
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry
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Catalysis
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Combinatorial Chemistry Techniques
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Cyclization
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Cycloparaffins / chemical synthesis*
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Cycloparaffins / chemistry
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Furans / chemical synthesis
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Furans / chemistry*
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Molecular Structure
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Stereoisomerism
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Titanium / chemistry*
Substances
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Alkanes
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Bridged Bicyclo Compounds, Heterocyclic
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Cycloparaffins
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Furans
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titanium tetrachloride
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Titanium
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nonane