Unprecedented chemoselective Ru(iii)-catalyzed [3+2] annulation of enaminones with iodonium ylides for the synthesis of functionalized 3a,7a-dihydroxy hexahydro-4H-indol-4-ones

Herein, a straightforward and efficient method to obtain 3a,7a-dihydroxy hexahydro-4H-indol-4-ones via Ru(iii)-catalyzed alkenyl C(sp(2))-H bond functionalization/[3 + 2] annulation of enaminones with iodonium ylides has been described. This protocol features chemoselectivity, broad substrate scope, moderate to excellent yields, gram-scale synthesis, and mild reaction conditions. The newly formed 3a,7a-dihydroxy hexahydro-4H-indol-4-one scaffolds can be easily further derivatized to 1H-pyrrol-3-ol carboxylate derivatives through an open-ring/hydrolysis transformation, showing potential applications in organic synthesis and medicinal chemistry.

Automated summary

Here, a straightforward method for obtaining 3a,7a-dihydroxy hexahydro-4H-indol-4-ones through Ru(III)-catalyzed alkenyl C(sp(2))-H bond functionalization/[3 + 2] annulation of enaminones with iodonium ylides is described. This protocol offers chemoselectivity, broad substrate scope, moderate to excellent yields, gram-scale synthesis, and mild reaction conditions. The resulting 3a,7a-dihydroxy hexahydro-4H-indol-4-one scaffolds can be easily further modified to 1H-pyrrol-3-ol carboxylate derivatives, showing potential applications in organic synthesis and medicinal chemistry.