Copper(I)-catalyzed chlorine atom transfer radical cyclization reactions of unsaturated alpha-chloro beta-keto esters.
Copper(I) chloride catalyzed chlorine atom transfer radical cyclization reactions of a series of olefinic alpha-chloro beta-keto esters were investigated. It was found that alpha-dichlorinated beta-keto esters were suitable substrates; the chlorine transfer mono or tandem radical cyclization reactions catalyzed by CuCl complex with bis(oxazoline) or bipyridine proceeded smoothly in dichloroethane at room temperature or 80 degrees C, providing cyclic and bicyclic compounds in moderate to high yield. [reaction: see text]
Yang
Dan
D
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China. yangdan@hku.hk
Yan
Yi-Long
YL
Zheng
Bao-Fu
BF
Gao
Qiang
Q
Zhu
Nian-Yong
NY
D002384:Catalysis; D002713:Chlorine / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis; D005609:Free Radicals; D010080:Oxazoles / Q000737:chemistry
D004952:Esters; D005609:Free Radicals; D010080:Oxazoles; C064210:oxazolidine; D002713:Chlorine; D003300:Copper; C029892:cupric chloride