Rh(I)-Catalyzed Regio- and Enantioselective Ring Opening of Vinyl Cyclopropanes
We describe a Rh(I) catalyzed asymmetric ring opening of <i>racemic</i> vinyl cyclopropanes using aryl boronic acids as C-nucleophiles. When ferrocene-based chiral bisphosphines are used as ligands, the products are obtained with regioselectivities typically 99:1 r.r. and ee's generally between 88 and 96%. A wide range of aryl boronic acids can be used, and the products can be converted into a variety of targets. Preliminary mechanistic studies indicate that Zn(OTf)<sub>2</sub> plays a significant role in the reaction by promoting rhodium-ligand complex formation and accelerating the reaction. We expect this method and these mechanistic insights to be useful in the development of new asymmetric methods.
Authors
- Stephen P. Fletcher (ORCID: https://orcid.org/0000-0001-7629-0997)
- Kirsten E. Christensen (ORCID: https://orcid.org/0000-0003-1683-2066)
- Stephen J. Webster (ORCID: https://orcid.org/0000-0002-2445-8417)
- Violeta Stojalnikova (ORCID: https://orcid.org/0000-0002-8717-8367)
- F. Wieland Goetzke (ORCID: https://orcid.org/0000-0002-8688-5609)
- Ke Liu (ORCID: https://orcid.org/0000-0003-1506-0586)
- Harold W. Mackenzie (ORCID: https://orcid.org/0000-0001-7575-2790)
- László B. Balázs
Institutions
- Mansfield University (US)
- University of Oxford (GB)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2024-08-20
- DOI
- https://doi.org/10.1021/jacs.4c09490
- Citations
- 14
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 3.50
Funders
- GlaxoSmithKline
- Vertex Pharmaceuticals
- Fonds National de la Recherche Luxembourg
- Syngenta International
- Engineering and Physical Sciences Research Council