128587-85-9Relevant academic research and scientific papers
Borane-Catalyzed Chemoselective and Enantioselective Reduction of 2-Vinyl-Substituted Pyridines
Hu, Chen-Yu,Li, Xiang,Liang, Xin-Shen,Liu, Ning,Tian, Jun-Jie,Tu, Xian-Shuang,Wang, Xiao-Chen,Yang, Zhao-Ying
, p. 18452 - 18456 (2020)
Herein, we report that highly chemoselective and enantioselective reduction of 2-vinyl-substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro-bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade process involving 1,4-hydroboration followed by transfer hydrogenation of a dihydropyridine intermediate. The retained double bond in the reduction products permits their conversion to natural products and other useful heterocyclic compounds by simple transformations.
[2+2] Photodimerization of Stilbazoles Promoted by Oxalic Acid in Suspension
Nguyen, Thanh Binh,Nguyen, Tuan Minh,Retailleau, Pascal
supporting information, p. 4682 - 4689 (2020/04/15)
In this study, a very simple technique to perform efficiently photodimerization of some vinylpyridines is reported. By irradiating a stirred mixture of several stilbazoles with solid oxalic acid dihydrate dispersed in a nonpolar (i.e., cyclohexane) or moderately polar (benzene, dichloromethane, dioxane) solvent, the corresponding dimeric cyclobutane adducts were obtained in high yields and excellent regio- and stereoselectivities. The strategy could also be applied successfully to oily, waxy, or even insoluble stilbazoles. Moreover, the oxalic acid loading could be lowered to substoichiometric amounts. When further optimizations were needed, our strategy was found to be highly flexible to identify other oligocarboxylic acids as alternative additives to improve, or even overturn, the regioselectivity. Oxalic acid and other oligocarboxylic acids were found to be capable of orienting more than 50 stilbazoles toward photodimerization under these conditions.
