Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • News & Views
  • Published:

Cross-coupling

Stereochemistry by remote control

The stereochemical lability of cycloalkylzinc reagents combined with a large difference in reactivity between epimers has been exploited to form a wide variety of interesting organic compounds with both high yields and diastereoselectivities.

This is a preview of subscription content, access via your institution

Access options

Buy this article

Prices may be subject to local taxes which are calculated during checkout

Figure 1: A simplified mechanistic scheme for highly diastereoselective Negishi couplings using a 1,4-substituted cycloalkylzinc reagent as an example.
Figure 2: The broad scope of the diastereoselective Negishi cross-coupling.

References

  1. Hayashi, T. J. Organomet. Chem. 653, 41–45 (2002).

    Article  CAS  Google Scholar 

  2. Glorius, F. Angew. Chem. Int. Ed. 47, 8347–8349 (2008).

    Article  CAS  Google Scholar 

  3. Rudolph, A. & Lautens, M. Angew. Chem. Int. Ed. 48, 2656–2670 (2009).

    Article  CAS  Google Scholar 

  4. Saito, B. & Fu, G. C. J. Am. Chem. Soc. 130, 6694–6695 (2008).

    Article  CAS  Google Scholar 

  5. Blaser, H.-U., Hoge, G., Pugin, B. & Spindler, F. in Green Catalysis (eds Anastas, P. T. & Crabtree, B.) Vol. 1, 153–203 (Wiley-VCH, 2009).

    Google Scholar 

  6. Thaler, T. et al. Nature Chem. 2, 125–130 10.1038/nchem.505(2010).

    Article  CAS  Google Scholar 

  7. Boudier, A. et al. Chem. Eur. J. 6, 2748–2761 (2000).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Glorius, F. Stereochemistry by remote control. Nature Chem 2, 78–80 (2010). https://doi.org/10.1038/nchem.528

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1038/nchem.528

Search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing