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Organocatalytic Enantioselective Synthesis of Polysubstituted Spirooxindoles using a Tandem Michael-Michael Reaction
S. Abbaraju, N. Ramireddy, , H. Arman, J.C.-G. Zhao
Published in Wiley-VCH Verlag
Volume: 357
Issue: 12
Pages: 2633 - 2638
A highly efficient stereoselective method for the synthesis of functionalized spirooxindole derivatives with four contiguous stereogenic centers, including two adjacent quaternary stereogenic centers, was realized through an organocatalytic tandem Michael-Michael reaction. By employing a quinidine-derived thiourea organocatalyst, the reaction between (E)-2-cyano-2-(2-oxo-1-tritylindolin-3-ylidene)acetates and (E)-1-alkyl-6-nitro-hex-2-en-1-ones yields the desired spirooxindole products in good yields (up to 90%) and with excellent stereoselectivities (up to 95:5 dr and 98% ee). © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
About the journal
JournalData powered by TypesetAdvanced Synthesis and Catalysis
PublisherData powered by TypesetWiley-VCH Verlag