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The inverted ketene synthon: a double umpolung approach to enantioselective β^2,3-amino amide synthesis.

ABSTRACT: A stereocontrolled synthesis of β^2,3-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 anti-β^2,3-amino amide with high selectivity.

SUBMITTER: Vishe M

PROVIDER: S-EPMC6349014 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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

Vishe Mahesh M Johnston Jeffrey N JN

Chemical science 20181112 4

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 anti-β2,3-amino amide with ...[more]

PMID: 30774911

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