Diastereoselective Three-Component 3,4-Amino Oxygenation of 1,3-Dienes Catalyzed by a Cationic Heptamethylindenyl Rhodium(III) Complex

The direct oxyamination of olefins is a compelling tool to rapidly access beta-amino alcohols-a privileged motif ubiquitous in natural products, pharmaceuticals and agrochemicals. Although a variety of expedient methods are established for simple alkenes, selective amino oxygenation of 1,3-dienes is less explored. Within this context, methods for the oxyamination of 1,3-dienes that are selective for the internal position remain unprecedented. We herein report a modular three-component approach to perform an internal and highly diastereoselective amino oxygenation of 1,3-dienes catalyzed by a cationic heptamethylindenyl (Ind*) Rh(III) complex.

Automated summary

A method for the internal and highly diastereoselective amino oxygenation of 1,3-dienes has been developed, catalyzed by a cationic heptamethylindenyl (Ind*) Rh(III) complex, filling the gap in the selective amino oxygenation of 1,3-dienes at the internal position.