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Synthetic methodology

Copper for alkynylallylic substitution

Chiral tetrahedral carbon atoms bearing functional groups amenable to functionalization offer numerous synthetic opportunities. Catalysed by copper pyridine-bis(oxazoline) complexes, the developed alkynylallylic substitution provides 3-substituted 1,4-enynes with excellent regio- and stereocontrol.

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Fig. 1: Enantioselective alkynylallylic substitution.


  1. Tsuji, J., Takahashi, H. & Morikawa, M. Tetrahedron Lett. 6, 4387–4388 (1965).

    Article  Google Scholar 

  2. Trost, B. M. & Fullerton, T. J. J. Am. Chem. Soc. 95, 292–294 (1973).

    Article  CAS  Google Scholar 

  3. Pàmies, O. et al. Chem. Rev. 121, 4373–4505 (2021).

    Article  Google Scholar 

  4. Tsuji, H. & Kawatsura, M. Asian J. Org. Chem. 9, 1924–1941 (2020).

    Article  CAS  Google Scholar 

  5. Ma, J.-S. et al. Nat. Synth. (2022).

    Article  Google Scholar 

  6. Lovering, F., Bikker, J. & Humblet, C. J. Med. Chem. 52, 6752–6756 (2009).

    Article  CAS  Google Scholar 

  7. Shi, X., Gorin, D. J. & Toste, F. D. J. Am. Chem. Soc. 127, 5802–5803 (2005).

    Article  CAS  Google Scholar 

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Correspondence to Jan H. van Maarseveen.

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van Maarseveen, J.H. Copper for alkynylallylic substitution. Nat. Synth 2, 11–12 (2023).

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