Highly enantioselective 1,3-dipolar cycloaddition of azomethine ylides catalyzed by copper(I)/TF-BiphamPhos complexes.
A new and highly efficient Cu(I)/TF-BiphamPhos catalytic system exhibited excellent reactivity, enantio-/diastereoselectivity, and structural scope in asymmetric 1,3-dipolar cycloaddition of azomethine ylides with 0.1-3 mol % of catalyst loading. The present methodology is the best result for asymmetric cycloaddition of azomethine ylides, especially derived from amino esters other than glycinate in terms of reactivity and enantioselectivity.
Wang
Chun-Jiang
CJ
College of Chemistry and Molecular Sciences, Wuhan University, PR China 430072. cjwang@whu.edu.cn
Liang
Gang
G
Xue
Zhi-Yong
ZY
Gao
Feng
F
D000596:Amino Acids / Q000737:chemistry; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002621:Chemistry / Q000379:methods*; D003300:Copper / Q000737:chemistry*; D046911:Macromolecular Substances / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D001391:Azo Compounds; D046911:Macromolecular Substances; D013882:Thiosemicarbazones; C512188:azomethine; D003300:Copper; D009584:Nitrogen