Gold(I)-Catalyzed Stereoconvergent, Intermolecular Enantioselective Hydroamination of Allenes


  • We thank the NIH (R01 GM080422-01) for support of this research. K.L.B. was supported in part through a Charles Bradsher Fellowship (Duke University) and M.T. was supported in part through a Marco Polo Fellowship (Alma Mater Studiorum—University of Bologna).


original image

Gold and silver: A 1:2 mixture of [{(S)-1}(AuCl)2] and AgBF4 catalyzes the enantioselective hydroamination of chiral, racemic 1,3-disubstituted allenes with N-unsubstituted carbamates to form N-allylic carbamates in good yield, with high regio- and diastereoselectivity, and up to 92 % ee (see scheme, Cbz=benzyloxycarbonyl).