Research news, Mar. 28th, 2014.

   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

 Fei Zhao, Yuexing Li, Yang Wang, Wen-Xiong Zhang,* and Zhenfeng Xi.

Org. Biomol. Chem. 2014, 12, 3336-3339. (Inside Front Cover)

Considerable efforts have been devoted to the dimerization of terminal alkynes because it provides a straightforward method to construct conjugated enynes, which are versatile building blocks in organic synthesis and significant components in bioactive molecules. As far as we are aware, the multicomponent coupling via incorporating organic components into the well-established dimerization of terminal alkynes is not reported. On the other hand, (Z)-enynols, as a class of multifunctional organic skeletons, are of considerable interest in modern organic synthesis because of their important application in synthesis of O-containing heterocycles. Although the synthesis of (Z)-enynols has received much interest, (Z)-enynols bearing a heteroatomic substituent at C1 position is not reported because of the difficulty in introducing a heteroatom into the starting materials. The paper featured on the cover of OBC provides the first synthesis of (Z)-enynols via Cu(I)-mediated (Z)-selective geminal coupling among two molecules of terminal alkynes, carbodiimides, and oxalyl chloride. Further transformation of the (Z)-enynol is performed to yield highly functionalized spiro heterocyclic compound.