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The inverted ketene synthon: a double umpolung approach to enantioselective β2,3-amino amide synthesis

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Abstract

A stereocontrolled synthesis of β2,3-amino amides is reported. Innovation is encapsulated by the first use of nitroalkenes to achieve double umpolung in enantioselective β-amino amide synthesis. Step economy is also fulfilled by the use of Umpolung Amide Synthesis (UmAS) in the second step, delivering the amide product without intermediacy of a carboxylic acid or activated derivative. Molybdenum oxide-mediated hydride reduction provides the anti2,3-amino amide with high selectivity.

Graphical abstract: The inverted ketene synthon: a double umpolung approach to enantioselective β2,3-amino amide synthesis

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Publication details

The article was received on 29 Sep 2018, accepted on 11 Nov 2018 and first published on 12 Nov 2018


Article type: Edge Article
DOI: 10.1039/C8SC04330B
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    The inverted ketene synthon: a double umpolung approach to enantioselective β2,3-amino amide synthesis

    M. Vishe and J. N. Johnston, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC04330B

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