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Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis

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Abstract

The first examples of ynamide hydroacylation are described. Using rhodium catalysis, linear β-enaminone products are generated in high yield and excellent regioselectivity from the combination of aldehydes and ynamides. The enaminone products are subsequently used as a platform to construct a diverse array of substituted pyrazoles, pyrimidines, and isoxazoles in a two-step, one-pot sequence. It was found that with judicious choice of catalyst system it was possible to overturn the regioselectivity of the hydroacylation reaction to generate α-enaminone products.

Graphical abstract: Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis

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Publication details

The article was received on 30 Aug 2017, accepted on 27 Sep 2017 and first published on 05 Oct 2017


Article type: Edge Article
DOI: 10.1039/C7SC03795C
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis

    Robert N. Straker, M. K. Majhail and M. C. Willis, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC03795C

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