Synthesis of enol lactones via Cu(I)-catalyzed intramolecular O-vinylation of carboxylic acids.
With the catalysis of CuI/trans-N,N'-dimethylcyclohexane-1,2-diamine, a number of carboxylic acids underwent efficient intramolecular O-vinylation with vinyl bromides leading to the synthesis of the corresponding five- and six-membered enol lactones. The same catalytic system also led to the efficient cycloisomerization of alkynoic acids.
Sun
Changhui
C
Department of Chemistry, Tongji University, 1239 Siping Road, Shanghai 200092, PR China.
Fang
Yewen
Y
Li
Shuang
S
Zhang
Yue
Y
Zhao
Qiwu
Q
Zhu
Shana
S
Li
Chaozhong
C
D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003959:Diamines / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry*
D002264:Carboxylic Acids; D003959:Diamines; D007783:Lactones; D013438:Sulfhydryl Compounds; D014753:Vinyl Compounds; C003763:vinyl bromide