Fig. 2. Substrate scope of the copper-catalyzed enantioselective hydroamination of internal olefins.

(A): Asymmetric hydroamination of 2-butene with a variety of electrophilic amines. (B): Scope of symmetrical internal olefins. (C): Deuterium Incorporation. (D): Regioselectivity in the hydroamination of unsymmetrical internal olefins. Yields refer to isolated yields on the average of two runs. Enantiomeric excesses were determined by chiral HLPC analysis or using Swager’s protocol (37). * Yield in parentheses was determined by ¹H NMR analysis. † Reaction was performed on a 5 mmol scale with 1 mol % Cu(OAc)₂, 1.1 mol % (S)-DTBM-SEGPHOS and 2 mol % PPh₃. ‡ Ph₂SiD₂ was used in lieu of (MeO)₂SiMeH. d.r. = diastereomeric ratio.