Enantioselective Synthesis of Spirooxindole Derivatives through Lewis Acid-Catalyzed Michael Addition/Cyclization
Fen Tan1,2, Zhou-Yang Xu1, Zhen Li1
1Hubei Key Laboratory of Purification and Application of Plant Anti-cancer Active Ingredients, School of Chemistry and Life Sciences, Hubei University of Education, Wuhan, Hubei 430205, P. R. of China.
Abstract:
A Mg(OTf)2-catalyzed asymmetric Michael addition/cyclization cascade reaction between 3-isothiocyanato oxindoles and 2-arylidene-1,3-indanediones has been developed. This transformation provides an efficient and concise approach to biologically important bispiro[indanedione-oxindole-pyrrolidinyl]s under mild conditions in good to excellent yields (70-99% yields) with moderate to good stereoselectivities (up to 99% ee and >95:5 d.r.). Notably, biological investigation reveals that one of the synthesized bispiro[indanedione-oxindole-pyrrolidinyl]s exhibits promising cytotoxicity against NCI-H460 human lung cancer and SW-620 human colon cancer cells.
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