Organocatalytic Asymmetric Domino Michael/Henry Reaction of Indolin-3-ones with o-Formyl-β-nitrostyrenes

Synthesis (Stuttg). 2015 Apr 1;47(7):1024-1031. doi: 10.1055/s-0034-1379943.

Abstract

A highly diastereo- and enantioselective domino Michael/Henry reaction of 1-acetylindolin-3-ones with o-formyl-(E)-β-nitrostyrenes catalyzed by low loading of a quinine-derived amine-squaramide provides the corresponding indolin-3-one derivatives bearing four adjacent stereogenic centers in good to high yields and with excellent stereoselectivities.

Keywords: domino reaction; indolin-3-one; organocatalysis; oxindole; squaramide.