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Issue 4, 2015
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Enantioselective synthesis of D-α-amino amides from aliphatic aldehydes

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Abstract

Peptides consisting of D-amino amides are highly represented among both biologically active natural products and non-natural small molecules used in therapeutic development. Chemical synthesis of D-amino amides most often involves approaches based on enzymatic resolution or fractional recrystallization of their diastereomeric amino acid salt precursors, techniques that produce an equal amount of the L-amino acid. Enantioselective synthesis, however, promises selective and general access to a specific α-amino amide, and may enable efficient peptide synthesis regardless of the availability of the corresponding α-amino acid. This report describes the use of a cinchona alkaloid-catalyzed aza-Henry reaction using bromonitromethane, and the integration of its product with umpolung amide synthesis. The result is a straightforward 3-step protocol beginning from aliphatic aldehydes that provides homologated peptides bearing an aliphatic side chain at the resulting D-α-amino amide.

Graphical abstract: Enantioselective synthesis of d-α-amino amides from aliphatic aldehydes

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Publication details

The article was received on 07 Jan 2015, accepted on 16 Feb 2015 and first published on 27 Feb 2015


Article type: Edge Article
DOI: 10.1039/C5SC00064E
Citation: Chem. Sci., 2015,6, 2590-2595
  • Open access: Creative Commons BY-NC license
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    Enantioselective synthesis of D-α-amino amides from aliphatic aldehydes

    K. E. Schwieter and J. N. Johnston, Chem. Sci., 2015, 6, 2590
    DOI: 10.1039/C5SC00064E

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