Asymmetric Suzuki-Miyaura coupling of heterocycles via Rhodium-catalysed allylic arylation of racemates

Philipp Schäfer, Thomas Palacin, Mireia Sidera and Stephen P. Fletcher ()
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Philipp Schäfer: Chemistry Research Laboratory, University of Oxford
Thomas Palacin: Chemistry Research Laboratory, University of Oxford
Mireia Sidera: Chemistry Research Laboratory, University of Oxford
Stephen P. Fletcher: Chemistry Research Laboratory, University of Oxford

Nature Communications, 2017, vol. 8, issue 1, 1-12

Abstract: Abstract Using asymmetric catalysis to simultaneously form carbon–carbon bonds and generate single isomer products is strategically important. Suzuki-Miyaura cross-coupling is widely used in the academic and industrial sectors to synthesize drugs, agrochemicals and biologically active and advanced materials. However, widely applicable enantioselective Suzuki-Miyaura variations to provide 3D molecules remain elusive. Here we report a rhodium-catalysed asymmetric Suzuki-Miyaura reaction with important partners including aryls, vinyls, heteroaromatics and heterocycles. The method can be used to couple two heterocyclic species so the highly enantioenriched products have a wide array of cores. We show that pyridine boronic acids are unsuitable, but they can be halogen-modified at the 2-position to undergo reaction, and this halogen can then be removed or used to facilitate further reactions. The method is used to synthesize isoanabasine, preclamol, and niraparib—an anticancer agent in several clinical trials. We anticipate this method will be a useful tool in drug synthesis and discovery.

Date: 2017
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DOI: 10.1038/ncomms15762

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