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2019-06-28b - Sulfamate_Giese_Manuscript - ChemRxiv.pdf (554.49 kB)
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Sulfamyl Radicals Direct Photoredox-Mediated Giese Reactions at Unactivated C(3)–H Bonds

preprint
revised on 28.06.2019 and posted on 01.07.2019 by Anastasia Gant Kanegusuku, Thomas Castanheiro, Suraj Ayer, Jennifer Roizen
This manuscript describes the use of alcohol-derived sulfamate ester anchors to guide the alkylation of aliphatic C(3)–H bonds in the course of Giese reactions. This reaction tolerates a large range of functional groups that are sensitive to oxidation. The developed reaction proceeds with predictable diastereoselectivity using enantioenriched radical acceptors, and complex small molecule substrates. Surprisingly, this transformation affects position-selective alkylation of tertiary and secondary centers with synthetically useful efficiencies.

Funding

National Institutes of Health (R35GM128741-01)

History

Email Address of Submitting Author

j.roizen@duke.edu

Institution

Duke University

Country

United States

ORCID For Submitting Author

0000-0002-6053-5512

Declaration of Conflict of Interest

no conflict of interest

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