Cs₂CO₃‐Promoted Michael Addition‐[2,3]‐Sigmatropic Rearrangement Domino Reaction: Facile Synthesis of a 3‐Substituted Indoles Bearing a Homoallyl Sulfide Moiety

Abstract

AC s 2 CO 3 -promoted Michael addition-[2,3]-sigmatropic rearrangement dominor eaction between arenesulfonylindolea nd sulfur ylide hasb een developed. This reaction affords af acile methodf or the synthesis of 3-substituted indoles with ah omoallyl sulfide moiety.I nt his domino sequence, two CÀCb onds and one CÀCb ond cleavage were formed.

Arenesulfonyl indole: new precursor for diversification of C-3 functionalized indoles

“…Du 66 et al, in 2016, developed a racemic Cs 2 CO 3 promoted Michael addition of sulfur ylides 94 to imine intermediate generated from arenesulfonyl indoles 11 followed by [2,3]sigmatropic rearrangement domino reaction to obtain 3substituted indoles 95 and 95 0 bearing a sulde moiety in good to high yields up to 89% (Scheme 32). According to the mechanism proposed by the author, the ylide 96 attacks on the vinylogous imine intermediate 2, generated in situ from one equivalent of Cs 2 CO 3 .…”