Transition metal-catalyzed regioselective and stereoselective aminochlorination of cinnamic esters

被引:102
作者
Li, GG [1 ]
Wei, HX [1 ]
Kim, SH [1 ]
Neighbors, M [1 ]
机构
[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
关键词
D O I
10.1021/ol990059e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A new aminohalogenation process has been developed for the synthesis of vicinal haloamine derivatives using cinnamic esters as substrates. The reaction was performed in CH3CN using ZnCl2 or Cu(OTf)(2) as catalyst and N,N-dichloro-p-toluenesulfonamide as chlorine/nitrogen source. Good to excellent yields and regio- and stereoselectivities have been obtained. The stereochemistry was unambiguously determined by transforming one of the products to a known sample.
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页码:395 / 397
页数:3
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