Diastereoselective Michael reaction of chiral nickel(II) glycinate with nitroalkenes for asymmetric synthesis of b-substituted a,c-diaminobutyric acid derivatives in water

Jiang Wang • Xun Ji • Jianmei Shi • Haifeng Sun • Hualiang Jiang • Hong Liu

Abstract We have developed the first operationally simple and environmentally benign protocol for the aque- ous asymmetric Michael addition reaction of chiral nick- el(II) glycinate with nitroalkenes. The reactions proceeded smoothly in the presence of TBAB (tetrabutyl ammonium bromide) in neat water at room temperature and provided good yields of b-substituted a,c-diaminobutyric acid derivatives with excellent diastereoselectivities.

Keywords Michael reaction 􏰒 Nickel(II) glycinate 􏰒 Asymmetric synthesis 􏰒 Diaminobutyric acids