Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles

[Image: see text] 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...

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Detalles Bibliográficos
Autores principales: Kang, Houng, Lee, Young Eun, Reddy, Peddiahgari Vasu Govardhana, Dey, Sangeeta, Allen, Scott E., Niederer, Kyle A., Sung, Paul, Hewitt, Kirsten, Torruellas, Carilyn, Herling, Madison R., Kozlowski, Marisa C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5654492/
https://www.ncbi.nlm.nih.gov/pubmed/29022352
http://dx.doi.org/10.1021/acs.orglett.7b02552
Descripción
Sumario:[Image: see text] 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.

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