1208117-74-1Relevant articles and documents
Catalytic C-CN activation and asymmetric cyanoamidation of alkenes: Total syntheses of (+)-horsfiline, (-)-coerulescine, and (-)-esermethole
Reddy, Venkata Jaganmohan,Douglas, Christopher J.
scheme or table, p. 4719 - 4729 (2010/08/06)
The detailed study of Pd-catalyzed asymmetric cyanoamidation is reported. Excellent enantioselectivities are attributed to a chiral phosphosphoramidite ligand synthesized in one step from the commercially available materials. Cyanoamidation substrates are easy to prepare from the corresponding anilines. The 3,3-disubstituted oxindole products bear all-carbon quaternary stereocenters and contain a nitrile and an amide, which are valuable functional handles for the synthesis of many indole-containing natural products. Cyanoamidation tolerates free N-H groups, as demonstrated by the successful use of cyanoamidation in the syntheses of (+)-horsfiline and (-)-coerulescine.
