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

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.

SUBMITTER: Straker RN

PROVIDER: S-EPMC5853270 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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

Straker Robert N RN Majhail Manjeet K MK Willis Michael C MC

Chemical science 20171005 12

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 regioselectivi ...[more]

PMID: 29568442

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