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Sulfamyl Radicals Direct Photoredox-Mediated Giese Reactions at Unactivated C(3)–H Bonds
preprintrevised on 28.06.2019, 16:57 and posted on 01.07.2019, 21:19 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.
Read the published paper
in Organic Letters