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Cinchona-based primary amine catalysis in the asymmetric functionalization of carbonyl compounds

Paolo Melchiorre1

  • 1ICREA-Institució Catalana de Recerca i Estudis Avançats, Passeig Lluís Companys 23, Barcelona, Spain. pmelchiorre@iciq.es

Angewandte Chemie (International Ed. in English)
|August 16, 2012
PubMed

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
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