Abstract
A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(II) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemical synthesis
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Aldehydes / chemistry
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Amino Acids / chemical synthesis*
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Amino Acids / chemistry
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Cyclohexenes / chemistry*
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Diazonium Compounds / chemical synthesis
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Diazonium Compounds / chemistry
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Esters / chemical synthesis
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Esters / chemistry
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Molecular Structure
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Tin Compounds / chemistry*
Substances
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Aldehydes
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Amino Acids
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Cyclohexenes
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Diazonium Compounds
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Esters
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Tin Compounds
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semipinacol
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stannous chloride
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diazoacetic ester