Rhodium‐Catalyzed Asymmetric Allenylation of Sulfonylimines and Application to the Stereospecific Allylic Allenylation

Abstract

Abstract The rhodium‐catalyzed asymmetric allenylation of sulfonylimines is disclosed providing silyl homoallenylamide products in up to 99:1 er . Through subsequent activation of the C−N bond of the silyl homoallenyl sulfonamide, palladium‐catalyzed stereospecific allylic allenylation could be achieved giving C−C bond formation with high chirality transfer. The synthetic utility of both the silyl homoallenyl sulfonamides and the silyl homoallenyl malonates as bis(nucleophiles) is demonstrated. magnified image