Abstract
Metal-free homoallylic oxygen-directed intramolecular hydroboration is reported. Regioselectivities from 20:1 to 82:1 favoring the 1,3-dioxy-substituted products have been achieved using Me2S.BH3/TfOH followed by standard oxidative workup. Branching at the C5 position improves regioselectivity.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Alcohols / chemistry*
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Alkenes / chemistry
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Boranes / chemistry*
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Iodine / chemistry
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Oxidation-Reduction
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Propanols / chemical synthesis
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Propanols / chemistry
Substances
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Alcohols
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Alkenes
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Boranes
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Propanols
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allyl alcohol
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Iodine