Enantioselective Rhodium-Catalyzed C–C Bond Activations

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.