22693-41-0Relevant articles and documents
Mechanistic Investigation and Optimization of Photoredox Anti-Markovnikov Hydroamination
Ganley, Jacob M.,Knowles, Robert R.,Nocera, Daniel G.,Qin, Yangzhong,Sun, Rui,Zhu, Qilei
supporting information, p. 10232 - 10242 (2021/07/26)
The reaction mechanism and the origin of the selectivity for the photocatalytic intermolecular anti-Markovnikov hydroamination of unactivated alkenes with primary amines to furnish secondary amines have been revealed by time-resolved laser kinetics measur
Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer
Zhu, Qilei,Graff, David E.,Knowles, Robert R.
supporting information, p. 741 - 747 (2018/01/26)
Here we report a catalytic method for the intermolecular anti-Markovnikov hydroamination of unactivated alkenes using primary and secondary sulfonamides. These reactions occur at room temperature under visible light irradiation and are jointly catalyzed by an iridium(III) photocatalyst, a dialkyl phosphate base, and a thiol hydrogen atom donor. Reaction outcomes are consistent with the intermediacy of an N-centered sulfonamidyl radical generated via proton-coupled electron transfer activation of the sulfonamide N-H bond. Studies outlining the synthetic scope (>60 examples) and mechanistic features of the reaction are presented.
A convergent asymmetric synthesis of γ-butenolides
Renard, Marc,Ghosez, Léon A.
, p. 2597 - 2608 (2007/10/03)
The addition of aldehydes to the new enantiomerically pure lithiated sulfoxide-orthoester 13 yielded γ-butenolides of high enantiomeric purities after elimination of phenylsulfinic acid. The cyclocondensation with ketones was less stereoselective. This new asymmetric synthesis of γ-butenolides has been applied to a convergent preparation of the antifungal antibiotic (+)-cerulenin.