Copper-catalyzed stereo- and chemoselective synthesis of enaminones via Michael type addition

Abstract

An efficient strategy for the synthesis of \(\upalpha \),\(\upbeta \)-unsaturated enaminones by the nucleophilic addition of N-heterocycles such as indole and imidazoles onto electronically bias alkynones under mild reaction conditions is described. Key feature of this reaction is the chemoselective addition of N-heterocycles onto ynones without affecting the \(1^{\mathrm{o}}\) amino groups (aromatic and aliphatic) of 5-aminoindole and tryptamine. The stereochemistry of the products was controlled by the tuning of reaction time. The mechanism of the reaction involves the Michael type addition of N-heterocycles on ynones via allene formation.

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Acknowledgements

We gratefully acknowledge the Council of Scientific and Industrial Research, India [02(0264)/16/EMR-II] for financial support and USIC, University of Delhi for providing instrumentation facilities. M.P. and Sushmita are thankful to DST-SERB and UGC, New Delhi for fellowships.

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Correspondence to Akhilesh Kumar Verma.

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Special Section on Transition Metal Catalyzed Synthesis of Medicinally Relevant Molecules

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Patel, M., Sushmita & Verma, A.K. Copper-catalyzed stereo- and chemoselective synthesis of enaminones via Michael type addition. J Chem Sci 130, 70 (2018). https://doi.org/10.1007/s12039-018-1465-9

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Keyword

  • Copper
  • alkynones
  • hydroamination
  • Michael addition
  • enaminones