ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
2 files

Catalytic Asymmetric Radical-Polar Crossover Hydroalkoxylation

preprint
revised on 21.10.2019, 19:25 and posted on 23.10.2019, 19:37 by Christopher Discolo, Eric Touney, Sergey Pronin
Asymmetric intramolecular hydrofunctionalization of tertiary allylic alcohols is described. This metal hydride-mediated catalytic radical-polar crossover reaction delivers corresponding epoxides in good to high enantioselectivity and constitutes the first example of asymmetric hydrogen atom transfer-initiated process. A series of modified cobalt salen complexes has proven optimal for achieving good efficiency and asymmetric induction. Experimental data suggest that cationic cobalt complexes are involved in enantio-determining step, where cation–π interactions in the catalyst contribute to the asymmetric induction.

Funding

CAREER CHE-1848076

PRF 58063-DNI1

History

Email Address of Submitting Author

spronin@uci.edu

Institution

The University of California, Irvine

Country

United States

ORCID For Submitting Author

0000-0002-0202-9232

Declaration of Conflict of Interest

The authors declare no competing financial interest

Exports