Enantioselective Organocatalytic Three-Component Vinylogous Michael/Aldol Tandem Reaction among 3‑Alkylidene oxindoles, Methyleneindolinones, and Aldehydes

We reported a one-pot enantioselective three-component vinylogous Michael/aldol tandem reaction of prochiral 3-alkylidene oxindoles with methyleneindolinones and aldehydes using bifunctional organocatalysts. A variety of enantioenriched 3,3-disubstituted oxindoles 3 and spirolactones 4 were generate...

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Veröffentlicht in:Journal of organic chemistry 2022-01, Vol.87 (1), p.197-210
Hauptverfasser: Xu, Jing-Xiang, Jiang, Yi-Syun, Chen, Chih-Hao, Sathishkumar, Nadaraj, Chu, Kai-Ti, Chiang, Ming-Hsi, Chen, Hsin-Tsung, Han, Jeng-Liang
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Sprache:eng
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Zusammenfassung:We reported a one-pot enantioselective three-component vinylogous Michael/aldol tandem reaction of prochiral 3-alkylidene oxindoles with methyleneindolinones and aldehydes using bifunctional organocatalysts. A variety of enantioenriched 3,3-disubstituted oxindoles 3 and spirolactones 4 were generated in moderate yields (up to 78%) with high stereoselectivities (up to >20:1 dr, >99% ee). Intriguingly, we observed that the aldol reaction with paraformaldehyde generates 3,3-disubstituted oxindoles 3 bearing a hydroxymethyl group, while the reaction with aliphatic aldehydes generates spirolactones 4.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02180