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Amide activation: an emerging tool for chemoselective synthesis

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Abstract

It is textbook knowledge that carboxamides benefit from increased stabilisation of the electrophilic carbonyl carbon when compared to other carbonyl and carboxyl derivatives. This results in a considerably reduced reactivity towards nucleophiles. Accordingly, a perception has been developed of amides as significantly less useful functional handles than their ester and acid chloride counterparts. However, a significant body of research on the selective activation of amides to achieve powerful transformations under mild conditions has emerged over the past decades. This review article aims at placing electrophilic amide activation in both a historical context and in that of natural product synthesis, highlighting the synthetic applications and the potential of this approach.

Graphical abstract: Amide activation: an emerging tool for chemoselective synthesis

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Publication details

The article was received on 27 Apr 2018 and first published on 28 Aug 2018


Article type: Review Article
DOI: 10.1039/C8CS00335A
Citation: Chem. Soc. Rev., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Amide activation: an emerging tool for chemoselective synthesis

    D. Kaiser, A. Bauer, M. Lemmerer and N. Maulide, Chem. Soc. Rev., 2018, Advance Article , DOI: 10.1039/C8CS00335A

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