Asymmetric Synthesis of Trifluoromethylated Allylic Amines Using α,<i>β</i>-Unsaturated <i>N</i>-<i>tert</i>-Butanesulfinimines

Abstract

[reaction: see text]. The trifluoromethide ion generated in situ from TMSCF(3) and TBAT (tetrabutylammonium triphenyldifluorosilicate), as well as TMAF (tetramethylammonium fluoride), adds to the alpha,beta-unsaturated N-tert-butanesulfinimines exclusively in a 1,2 fashion with high diastereoselectivities, affording the first examples of chiral trifluoromethylated allylic amines.