191725-63-0Relevant academic research and scientific papers
Copper-catalyzed vinylogous aerobic oxidation of unsaturated compounds with air
Zhang, Hai-Jun,Schuppe, Alexander W.,Pan, Shi-Tao,Chen, Jin-Xiang,Wang, Bo-Ran,Newhouse, Timothy R.,Yin, Liang
, p. 5300 - 5310 (2018)
A mild and operationally simple copper-catalyzed vinylogous aerobic oxidation of β,γ- and α,β-unsaturated esters is described. This method features good yields, broad substrate scope, excellent chemo- and regioselectivity, and good functional group tolerance. This method is additionally capable of oxidizing β,γ- and α,β-unsaturated aldehydes, ketones, amides, nitriles, and sulfones. Furthermore, the present catalytic system is suitable for bisvinylogous and trisvinylogous oxidation. Tetramethylguanidine (TMG) was found to be crucial in its role as a base, but we also speculate that it serves as a ligand to copper(II) triflate to produce the active copper(II) catalyst. Mechanistic experiments conducted suggest a plausible reaction pathway via an allylcopper(II) species. Finally, the breadth of scope and power of this methodology are demonstrated through its application to complex natural product substrates.
Asymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis
Su, Yong-Liang,Li, Lu-Lu,Zhou, Xiao-Le,Dai, Zhen-Yao,Wang, Pu-Sheng,Gong, Liu-Zhu
supporting information, p. 2403 - 2406 (2018/04/27)
A palladium-catalyzed asymmetric α-allylation of aldehydes with alkynes has been established by integrating the catalysis of enamine and chiral hydridopalladium complex that is reversibly formed from the oxidative addition of Pd(0) to chiral phosphoric acid. The ternary catalyst system, consisting of an achiral palladium complex, a primary amine, and a chiral phosphoric acid allows the reaction to tolerate a wide scope of α,α-disubstituted aldehydes and alkynes, affording the corresponding allylation products in high yields and with excellent levels of enantioselectivity.
Effective construction of quaternary stereocenters by highly enantioselective α-amination of branched aldehydes
Fu, Ji-Ya,Xu, Xiao-Ying,Li, Yan-Chun,Huang, Qing-Chun,Wang, Li-Xin
supporting information; experimental part, p. 4524 - 4526 (2010/11/21)
A highly efficient enantioselective α-amination of branched aldehydes with azadicarboxylates promoted by chiral proline-derived amide thiourea bifunctional catalysts was developed for the first time, affording the adducts bearing quaternary stereogenic centers with excellent yields (up to 99%) and enantioselectivities (up to 97% ee).
