Abstract
The first asymmetric γ-alkoxyallylboration of representative ketones provides β-alkoxy tert-homoallylic alcohols 10 whose diastereoselectivities range from 99% syn (acetophenone) to 99% anti (pinacolone) both with high ee (>95%). This distribution is attributable to the c/t isomerization of the BBD reagents and the greater reactivity of 7 vs 1 and of aromatic vs alkyl ketones. A ketone-based direct synthesis of a fostriecin intermediate and the tert-amine 26 are reported, each with high selectivities.
Publication types
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Alcohols / chemical synthesis*
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Alcohols / chemistry
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Amines / chemistry*
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Boranes / chemistry*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry*
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Catalysis
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Imines / chemistry*
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Ketones / chemistry*
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Molecular Structure
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Nitriles / chemistry*
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Polyenes / chemical synthesis
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Polyenes / chemistry
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Pyrones / chemical synthesis
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Pyrones / chemistry
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Stereoisomerism
Substances
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Alcohols
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Amines
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Boranes
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Bridged Bicyclo Compounds, Heterocyclic
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Imines
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Ketones
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Nitriles
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Polyenes
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Pyrones
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ketimine
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fostriecin