Accessing 4-oxy-substituted Isoquinolinones via C–H Activation and Regioselective Migratory Insertion with Electronically Biased ynol Ethers

Authors

Brandon L. Coles-Taylor, University of Denver
Maximilian S. McCallum, University of Denver
J. Scott Lee, University of Colorado
Brian W. Michel, University of DenverFollow

Publication Date

11-14-2018

Document Type

Article

Organizational Units

College of Natual Science and Mathematics, Chemistry and Biochemistry

Keywords

Ynol ethers, Regioselectivity, Migratory insertion

Abstract

The rhodium-catalyzed C–H activation and annulation with ynol ethers to directly provide 4-oxy substituted isoquinolinones is reported. The polarized nature of ynol ethers provides an electronic bias for controlling the regioselectivity of the migratory insertion process. While the highly reactive nature of ynol ethers presents a challenge, mild conditions were found to provide product in moderate to good yield. Utility was demonstrated by application in the synthesis of a prolyl-4-hydroxylase inhibitor framework.

Publication Statement

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Recommended Citation

Coles-Taylor, B. L., McCallum, M. S., Lee, J. S., & Michel, B. W. (2018). Accessing 4-oxy-substituted isoquinolinones via C–H activation and regioselective migratory insertion with electronically biased ynol ethers. Organic & Biomolecular Chemistry, 16(44), 8639-8646. DOI: 10.1039/c8ob02622j.