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Asymmetric catalysis

Selecting one out of six stereoisomers

The design of an original molecular architecture featuring an unusual sterically congested C(sp2)–C(sp3) stereogenic axis with six high rotational barriers results in the formation of six stereoisomers. The configuration of this axis can be controlled by transition metal catalysis and one stereoisomer can be produced selectively.

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Fig. 1: Catalyst control over higher-order stereogenicity.

References

  1. Le Bel, J. A. Bull. Soc. Chim. Fr. 22, 337–347 (1874).

    Google Scholar 

  2. van ’t Hoff, J. H. Archs. Neerland. Sci. Exactes et Naturelles 9, 445–454 (1874).

    Google Scholar 

  3. Grossman, R. B. J. Chem. Educ. 66, 30–33 (1989).

    Article  CAS  Google Scholar 

  4. Blaser, H. U. & Federsel, H.-J. (eds) In Asymmetric Catalysis on Industrial scale: Challenges, Approaches and Solutions 2nd edn (Wiley-VCH, 2010).

  5. Cheng, J. K., Xiang, S.-H., Li, S., Ye, L. & Tan, B. Chem. Rev. 121, 4805–4902 (2021).

    Article  CAS  Google Scholar 

  6. Wu, X. et al. Nat. Catal. https://doi.org/10.1038/s41929-021-00615-z (2021).

  7. Nakamura, M. & Ōki, M. Bull. Chem. Soc. Jpn. 48, 2106–2111 (1975).

    Article  CAS  Google Scholar 

  8. He, Q.-F. et al. J. Org. Chem. 86, 5870–5882 (2021).

    Article  CAS  Google Scholar 

  9. Krautwald, S. & Carreira, E. M. J. Am. Chem. Soc. 139, 5627–5639 (2017).

    Article  CAS  Google Scholar 

Download references

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Correspondence to Damien Bonne or Jean Rodriguez.

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Bonne, D., Rodriguez, J. Selecting one out of six stereoisomers. Nat Catal 4, 451–452 (2021). https://doi.org/10.1038/s41929-021-00639-5

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