Enantioselective Organocatalytic
Three-Component Vinylogous
Michael/Aldol Tandem Reaction among 3‑Alkylidene oxindoles,
Methyleneindolinones, and Aldehydes
posted on 2021-12-09, 18:05authored byJing-Xiang Xu, Yi-Syun Jiang, Chih-Hao Chen, Nadaraj Sathishkumar, Kai-Ti Chu, Ming-Hsi Chiang, Hsin-Tsung Chen, Jeng-Liang Han
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.