Abstract
A highly enantioselective trapping of protic phosphoramidate ammonium ylides with α-imino esters is reported. The intriguing Rh2(OAc)4 and chiral Brønsted acid co-catalyzed three-component Mannich-type reaction of a diazo compound, a phosphoramidate, and an α-imino ester provides a rapid and efficient access to 2,3-diaminosuccinic acid derivatives with a high level control of diastereo- and enantioselectivity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amides / chemistry*
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Amino Acids, Diamino / chemical synthesis
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Amino Acids, Diamino / chemistry*
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Azo Compounds / chemistry
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Catalysis
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Coordination Complexes / chemistry
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Crystallography, X-Ray
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Esters
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Imines / chemistry*
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Molecular Conformation
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Phosphoric Acids / chemistry*
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Quaternary Ammonium Compounds / chemistry*
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Rhodium / chemistry
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Stereoisomerism
Substances
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Amides
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Amino Acids, Diamino
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Azo Compounds
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Coordination Complexes
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Esters
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Imines
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Phosphoric Acids
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Quaternary Ammonium Compounds
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diaminosuccinic acid
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phosphoramidic acid
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Rhodium