Simple pyrrolidine-azole conjugates have been synthesized and found to be efficient catalysts for asymmetric Michael addition to nitrostyrenes. The identified optimal catalysts, pyrrolidine-azoles 2, 8 and 13, could catalyze the asymmetric Michael addition of a range of Michael donors and nitrostyrenes in high yields (up to 99%) and excellent stereoselectivities (up to 99:1 dr and 97% ee).
A simple primary-tertiary diamine has been explored as a novel catalyst for the Morita-Baylis-Hillman reaction of MVK and aryl aldehydes, and moderate to good chemical yields were obtained. Detailed mechanism study indicated that the diamine acted as a bifunctional cooperation catalyst via a bicyclic enamino-quaternary ammonium intermediate.
