Abstract
Enantiomerically pure fluorinated isoindoline and dihydroisoquinoline scaffolds have been prepared through a diastereoselective addition of fluorinated nucleophiles to Ellman's N-(tert-butanesulfinyl)imines followed by a sequence of Sonogashira cross-coupling/gold(I)-catalyzed cycloisomerization of the corresponding carbamate. A more favored 5-exo-dig mechanism was observed mainly due to an electronic effect of the fluorinated group.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amines / chemistry
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Carbamates / chemistry*
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Catalysis
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Gold / chemistry*
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Hydrocarbons, Fluorinated / chemical synthesis*
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Hydrocarbons, Fluorinated / chemistry
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Isoindoles / chemical synthesis*
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Isoindoles / chemistry
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Isoquinolines / chemical synthesis*
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Isoquinolines / chemistry
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Molecular Structure
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Stereoisomerism
Substances
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Amines
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Carbamates
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Hydrocarbons, Fluorinated
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Isoindoles
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Isoquinolines
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Gold