Abstract
Azomethine ylides are accessed under mild conditions via benzoic acid catalyzed condensations of 1,2,3,4-tetrahydroisoquinolines or tryptolines with aldehydes bearing a pendent dipolarophile. These intermediates undergo intramolecular [3 + 2]-cycloadditions in a highly diastereoselective fashion to form polycyclic amines with four new stereogenic centers. Challenging substrates such as piperidine, morpholine, and thiomorpholine undergo the corresponding reactions at elevated temperatures.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry
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Amines / chemical synthesis
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Amines / chemistry*
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Azo Compounds / chemical synthesis*
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Azo Compounds / chemistry
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Benzoic Acid / chemistry*
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Catalysis
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Cyclization
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Cycloaddition Reaction
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Molecular Structure
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Oxidation-Reduction
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Stereoisomerism
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Tetrahydroisoquinolines / chemistry*
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Thiosemicarbazones / chemical synthesis*
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Thiosemicarbazones / chemistry
Substances
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Aldehydes
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Amines
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Azo Compounds
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Heterocyclic Compounds, 4 or More Rings
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Tetrahydroisoquinolines
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Thiosemicarbazones
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azomethine
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Benzoic Acid