Selective synthesis of (Z)-2-enynyl-2-hydroxy-imidazolidine-4,5-diones via Cu(I)-mediated multicomponent coupling of terminal alkynes, carbodiimides and oxalyl chloride.
(Z)-2-Enynyl-2-hydroxy-imidazolidine-4,5-diones 2 are synthesized for the first time via Cu(I)-mediated (Z)-selective geminal coupling among two molecules of terminal alkynes, carbodiimides, and oxalyl chloride. Further transformation of 2a is performed to yield a highly functionalized spiro heterocyclic compound 5.
Beijing National Laboratory for Molecular Sciences, and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China. wx_zhang@pku.edu.cn.
Fei
F
Zhao
Yuexing
Y
Li
Yang
Y
Wang
Wen-Xiong
WX
Zhang
Zhenfeng
Z
Xi
D000480:Alkynes / Q000737:chemistry*; D002234:Carbodiimides / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D048289:Imidazolidines / Q000138:chemical synthesis* / Q000737:chemistry; D010070:Oxalates / Q000737:chemistry*
D000480:Alkynes; D002234:Carbodiimides; D002712:Chlorides; D048289:Imidazolidines; D010070:Oxalates; D003300:Copper; C092266:oxalyl chloride