Abstract
Acid treatment of densely substituted 2-silyl-1,2-dihydropyridines provides a new and convenient entry to reactive azomethine ylides that can (1) be protonated and reduced with high stereoselectivity to give piperidines, (2) participate in [3 + 2] dipolar cycloaddition to give tropanes, and (3) undergo a Nazarov-like 6-π electrocyclization that upon reduction give 2-azabicyclo[3.1.0] systems.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Aza Compounds / chemical synthesis*
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Aza Compounds / chemistry
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Azo Compounds / chemistry*
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Bridged Bicyclo Compounds / chemical synthesis*
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Bridged Bicyclo Compounds / chemistry
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Cyclization
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Magnetic Resonance Spectroscopy
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Piperidines / chemical synthesis*
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Piperidines / chemistry
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Stereoisomerism
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Thiosemicarbazones / chemistry*
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Tropanes / chemical synthesis*
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Tropanes / chemistry
Substances
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Aza Compounds
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Azo Compounds
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Bridged Bicyclo Compounds
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Piperidines
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Thiosemicarbazones
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Tropanes
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azomethine