Asymmetric Synthesis of Spirooxindoles with Seven Stereocenters via Organocatalyzed One‐pot Three‐component Sequential Cascade Reactions

A bifunctional squaramide‐catalyzed one‐pot three‐component Michael/Mannich‐Michael/cyclization sequential cascade reaction for the construction of bispirooxindole‐spirooxindoles was developed in good yields with excellent stereoselectivities (up to >20:1 dr, 99% ee). A series of original cinnamo...

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Veröffentlicht in:Advanced synthesis & catalysis 2019-07, Vol.361 (14), p.3412-3419
Hauptverfasser: Zhao, Bo‐Liang, Du, Da‐Ming
Format: Artikel
Sprache:eng
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Zusammenfassung:A bifunctional squaramide‐catalyzed one‐pot three‐component Michael/Mannich‐Michael/cyclization sequential cascade reaction for the construction of bispirooxindole‐spirooxindoles was developed in good yields with excellent stereoselectivities (up to >20:1 dr, 99% ee). A series of original cinnamoyl‐3‐ylideneoxindoles have been applied to this sequential cascade strategy for the first time. This new strategy provides a process for the enantioselective construction of bispirooxindole‐spirooxindoles with seven stereocenters, of which three are quaternary spiro‐stereocenters.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900218