Application Of Bifunctional Thiourea Catalyzed Asymmetric Michael Addition In The Construction Of The Quaternary Stereocenters Of2,2-disubstituted Oxindole And The Total Synthesis Of Morphine

Since the discovery to now, organocatalysis has always attract the interesting of many chemists. Based on our previous experience, We developed a useful asymmetric Michael reaction between2-substituted oxindoles and nitroolefins. A series of valuable2,2-disubstituted indolin-3-one derivatives were synthesized in high yields and the chiral quaternary-tertiary stereocenters were constructed with excellent stereoselectivities. Simple derivatization of the Michael adducts offered Pyrrolo[3,2-b]indole compounds. These compounds are all important subunits of natural products. In addition, we also probed the application of this method in the synthesis of morphine alkaloid.