4528-19-2Relevant articles and documents
Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer
Knowles, Robert R.,Metrano, Anthony J.,Tsuchiya, Yuto,Tsui, Elaine
supporting information, p. 11845 - 11849 (2020/05/22)
We report a catalytic, light-driven method for the intramolecular hydroetherification of unactivated alkenols to furnish cyclic ether products. These reactions occur under visible-light irradiation in the presence of an IrIII-based photoredox catalyst, a Br?nsted base catalyst, and a hydrogen-atom transfer (HAT) co-catalyst. Reactive alkoxy radicals are proposed as key intermediates, generated by direct homolytic activation of alcohol O?H bonds through a proton-coupled electron-transfer mechanism. This method exhibits a broad substrate scope and high functional-group tolerance, and it accommodates a diverse range of alkene substitution patterns. Results demonstrating the extension of this catalytic system to carboetherification reactions are also presented.
Stereoselective Synthesis of cis-2,5-Disubstituted Pyrrolidines via Copper-Catalyzed Cyclization of Alkenes
Cai, Sai-Hu,Da, Bing-Chao,Zhou, Jia-Hui,Xu, Yun-He,Loh, Teck-Peng
supporting information, p. 1076 - 1080 (2016/11/25)
An efficient methodology for the stereoselective synthesis of cis-2,5-disubstituted pyrrolidines using copper catalyst was developed. The corresponding cis-2,5-disubstituted pyrrolidines could be obtained in reasonable yields and with good stereoselectivities in the presence of 4,4′-di-tert-butyl-2,2′-bipyridine as ligand and 1-methyl-2-pyrrolidinone as solvent.
Lithiated carbamates: Chiral carbenoids for iterative homologation of boranes and boronic esters
Stymiest, Jake L.,Dutheuil, Guillaume,Mahmood, Adeem,Aggarwal, Varinder K.
, p. 7491 - 7494 (2008/09/17)
(Chemical Equation Presented) Take your pick: Either enantiomer of either diastereomer of substrates bearing adjacent stereogenic centers is accessible through reaction of an (R)- or (S)-lithiated carbamate with an (R)- or (S)-boronic ester (see scheme; pin = pinacolate, OCb = substituted carbamate).