Abstract
[reaction: see text] The stereoselective synthesis of novel alpha-epoxy-beta-amino acids is described by a route that combines the chemistry of oxazolinyloxiranyllithiums with that of nitrones. The intermediate trioxadiazadispiro[2.0.4.3]undecanes 4 have been isolated and converted by hydrolysis into epoxy-5-isoxazolidinones 5 which can be transformed into the alpha-epoxy-beta-amino acids 8 by N-O reduction.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amino Acids / chemical synthesis*
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Amino Acids / chemistry
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Epoxy Compounds / chemical synthesis*
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Lithium / chemistry*
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Nitrogen Oxides / chemistry
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Organometallic Compounds / chemistry*
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Oxazolidinones / chemistry*
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Oxidation-Reduction
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Stereoisomerism
Substances
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Amino Acids
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Epoxy Compounds
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Nitrogen Oxides
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Organometallic Compounds
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Oxazolidinones
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Lithium