Copper-catalyzed [4 + 1] cycloadditions of alpha,beta-acetylenic ketones with diazoacetates to form trisubstituted furans.
Copper-catalyzed [4 + 1] cycloaddition reaction of alpha,beta-acetylenic ketones with alpha-diazo esters offers an efficient, direct route to highly substituted furans. The reaction conditions and the scope of the process are examined, and a possible mechanism is proposed.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PRC.
Lian-Biao
LB
Zhao
Zheng-Hui
ZH
Guan
Yao
Y
Han
Yong-Xin
YX
Xie
Sheng
S
He
Yong-Min
YM
Liang
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D003979:Diazonium Compounds / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000480:Alkynes; D003979:Diazonium Compounds; D005663:Furans; D007659:Ketones; D003300:Copper; C032111:diazoacetic ester