3 years ago

Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles

Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles
Peddiahgari Vasu Govardhana Reddy, Madison R. Herling, Marisa C. Kozlowski, Young Eun Lee, Kyle A. Niederer, Houng Kang, Carilyn Torruellas, Scott E. Allen, Paul Sung, Sangeeta Dey, Kirsten Hewitt
The first examples of asymmetric oxidative coupling of simple phenols and 2-hydroxycarbazoles are outlined. Generation of a more vanadium catalyst by ligand design and by addition of an exogenous Brønsted or Lewis acid was found to be key to coupling the more oxidatively resistant phenols. The resultant vanadium complex is both more Lewis acidic and more strongly oxidizing. Good to excellent levels of enantioselectivity could be obtained, and simple trituration readily provided the products with ≥95% ee.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02552

DOI: 10.1021/acs.orglett.7b02552

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