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Pd(II)-Catalyzed Asymmetric Oxidative 1,2-Diamination of Conjugated Dienes with Ureas. 2018

Min-Song Wu, and Tao Fan, and Shu-Sen Chen, and Zhi-Yong Han, and Liu-Zhu Gong
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry , University of Science and Technology of China , Hefei 230026 , China.

A palladium(II)-catalyzed asymmetric 1,2-diamination of 1,3-dienes with readily available dialkylureas was established by using a chiral pyridine-oxazoline ligand. The diamination reaction exclusively occurs at the terminal C-C double bond of the 1,3-dienes to give 4-vinylimidazolidin-2-ones in high yields and with excellent levels of enantioselectivity (up to 99% yield, 97% ee). The reaction could feasibly be applied for gram-scale synthesis with a 1:1 ratio of the diene and the urea.

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