Design And Synthesis Of The Chiral Small-molecule Organocatalysts For The Asymmetric Michael Addition

The Michael reaction is widely recognized as one of the most important carbon-carbon bond-forming reactions in organic synthesis. Recently small-molecule organocatalysts for the asymmetric reaction have been widely and deeply studied. In this dissertation, we have synthesized a series of chiral ethers organocatalysts applied in asymmetric Michael addition. Detailed experiments which have been examined shown that the reaction was catalyzed by prolinol t-butyldiphenylsilyl ether as organocatalyst in nonpolar solvent, such as hexane, at 10℃for about 70 h, good yield and high diastereo- and enantioselectivities could be obtained. With the optimal condition, we have performed a variety of carbonyl compounds and nitroolefins as the substrates for the Michael addition and obtained excellent results. Prolinol silyl ether as catalyst has obviously virtue. It could be obtained by one step from prolinol with high yield.