Asymmetric Catalytic Double Michael Additions for the Synthesis of Spirooxindoles

作者:Kang, Tengfei; Zhao, Peng; Yang, Jian; Lin, Lili; Feng, Xiaoming; Liu, Xiaohua*
来源:Chemistry - A European Journal, 2018, 24(15): 3703-3706.
DOI:10.1002/chem.201800043

摘要

Asymmetric cascade double Michael additions to construct 2'-substituted 3,3'-spirooxindoles by using a chiral guanidine organocatalyst has been developed. A series of spirooxindole derivatives containing dihydrofuran or pyrrolidine subunits were obtained with good to excellent diastereo- and enantioselectivities. The method showed great tolerance of a number of aromatic and aliphatic alkynones. The strategy gave access to the asymmetric synthesis of (-)-salacin for the first time.