1282040-36-1Relevant academic research and scientific papers
Regioselective cobalt-catalyzed formation of bicyclic 3- and 4-aminopyridines
Garcia, Pierre,Evanno, Yannick,George, Pascal,Sevrin, Mireille,Ricci, Gino,Malacria, Max,Auber, C. Torinne,Gandon, Vincent
, p. 2030 - 2033 (2011)
Bimolecular cobalt-catalyzed [2+2+2] cycloadditions between yne-ynamides and nitriles afford bicyclic 3- or 4-aminopyridines in up to 100% yield. The high regioselectivity observed depends on the substitution pattern at the starting ynamide. Aminopyridines bearing TMS and Ts groups are efficiently deprotected in an orthogonal fashion.
Catalytic Asymmetric Three-component Hydroacyloxylation/ 1,4-Conjugate Addition of Ynamides
Cao, Weidi,Feng, Xiaoming,Jiang, Mingyi,Li, Xiangqiang,Zhan, Tangyu
, (2020/06/17)
A highly enantioselective three-component hydroacyloxylation/1,4-conjugate addition of ortho-hydroxybenzyl alcohols, ynamides and carboxylic acids was developed under mild reaction conditions in the presence of a chiral N,N′-dioxide/Sc(OTf)3 complex, which went through in situ generated ortho-quinone methides with α-acyloxyenamides, delivering a range of corresponding chiral α-acyloxyenamides derivatives containing gem(1,1)-diaryl skeletons in moderate to good yields with excellent ee values. The scale-up experiment and further derivation showed the practicality of this catalytic system. In addition, a possible catalytic cycle and transition state model was proposed to elucidate the origin of the stereoselectivity based on X-ray crystal structure of the α-acyloxyenamide intermediate and product.
