Rhodium-Catalyzed Asymmetric 1,4-Addition of α/β-(N-Indolyl) Acrylates

A rhodium-catalyzed asymmetric 1,4-addition of alpha/beta-(N-indolyl) acrylates to access highly enantioenriched chiral N- alkylindoles promoted by chiral diene or sulfur-olefin ligands under mild reaction conditions has been developed, which provides an efficient and practical approach for constructing carbon stereocenters adjacent to the indole nitrogen. The reaction can be applied to various N-indolyl-substituted alpha,beta-unstaturated esters and arylboron reagents, providing access to a wide range of alpha- and beta-(N- indolyl) propionate derivatives in high yields with excellent enantioselectivities (& LE;99% ee).

Automated summary

A rhodium-catalyzed asymmetric 1,4-addition reaction provides a practical approach for synthesizing highly enantioenriched chiral N-alkylindoles.