Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer | Zendy

Casey B. Roos | Zendy; Joachim Demaerel | Zendy; David Graff | Zendy; Robert R. Knowles | Zendy

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Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer

Author(s) -

Casey B. Roos,

Joachim Demaerel,

David Graff,

Robert R. Knowles

Publication year - 2020

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.0c01332

Subject(s) - chemistry , hydroamination , enantioselective synthesis , intramolecular force , proton coupled electron transfer , non covalent interactions , electron transfer , sulfonamide , radical , stereoselectivity , proton , photochemistry , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , molecule , hydrogen bond , physics , quantum mechanics

An enantioselective, radical-based method for the intramolecular hydroamination of alkenes with sulfonamides is reported. These reactions are proposed to proceed via N -centered radicals formed by proton-coupled electron transfer (PCET) activation of sulfonamide N-H bonds. Noncovalent interactions between the neutral sulfonamidyl radical and a chiral phosphoric acid generated in the PCET event are hypothesized to serve as the basis for asymmetric induction in a subsequent C-N bond forming step, achieving selectivities of up to 98:2 er. These results offer further support for the ability of noncovalent interactions to enforce stereoselectivity in reactions of transient and highly reactive open-shell intermediates.

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