Enantioselective Rhodium-Catalyzed C–C Bond Activations

Authors

  • Tobias Seiser
  • Nicolai Cramer Laboratorium für Organische Chemie, ETH Zürich, HCI H 304, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich

DOI:

https://doi.org/10.2533/chimia.2010.153

Keywords:

Asymmetric catalysis, C-c activation, C-h activation, Rhodium, Ring expansion

Abstract

The catalytic activation of carbon–carbon single bonds represents a major challenge in organometallic chemistry. Strained ring substrates occupy in this respect a privileged role as their inherent ring strain facilitates the desired metal insertion. Employing symmetrically substituted tert-cyclobutanols, an enantioselective rhodium(i)-catalyzed ?-carbon elimination creates alkyl-rhodium species bearing all-carbon quaternary stereogenic centers. Downstream reactions enable access to a wide range of synthetically versatile products such as substituted cyclohexenones, lactones and indanols with excellent enantioselectivities of up to 99% ee.

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Published

2010-03-31