Enantioselective Synthesis of Spirooxindole Derivatives through Lewis Acid-Catalyzed Michael Addition/Cyclization Cascade.

J Org Chem

Department of Radiation and Medical Oncology, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, P. R. of China.

Published: September 2025


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Article Abstract

A Mg(OTf)-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% 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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http://dx.doi.org/10.1021/acs.joc.5c01565DOI Listing

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