Abstract
A highly regio- and diastereoselective synthesis of bicyclic pyrazolidinone derivatives by rhodium(II) acetate catalyzed [3 + 3]-annulation with enoldiazoacetates and azomethine imines has been achieved in high yield. A vinylogous reaction of the metal enol carbene with the azomethine imine initiates [3 + 3]-cycloaddition, whereas reaction at the carbene center effects N-N-cleavage of the azomethine imine.
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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Azo Compounds / chemistry*
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry
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Catalysis
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Cyclization
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Cycloaddition Reaction
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Imines / chemistry*
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Methane / analogs & derivatives
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Methane / chemistry
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Molecular Structure
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Pyrazoles / chemical synthesis
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Pyrazoles / chemistry*
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Rhodium / chemistry
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Stereoisomerism
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Thiosemicarbazones / chemistry*
Substances
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Azo Compounds
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Bridged Bicyclo Compounds, Heterocyclic
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Imines
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Pyrazoles
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Thiosemicarbazones
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azomethine
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carbene
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Rhodium
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Methane