%0 Generic
%A Martjuga, Marina
%A Shabashov, Dmitry
%A Belyakov, Sergey
%A Liepinsh, Edvards
%A Suna, Edgars
%D 2010
%T Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of Enantiopure N-tert-Butanesulfinylketimines: Unusual Directing Effects of the ortho-Substituent
%U https://acs.figshare.com/articles/dataset/Asymmetric_Synthesis_of_1_3_Diamines_by_Diastereoselective_Reduction_of_Enantiopure_i_N_i_i_tert_i_Butanesulfinylketimines_Unusual_Directing_Effects_of_the_i_ortho_i_Substituent/2780332
%R 10.1021/jo100173f.s016
%2 https://ndownloader.figshare.com/files/4474744
%K Diastereoselective Reduction
%K Z geometry
%K Asymmetric Synthesis
%K Unusual Directing Effects
%K diastereoselective reduction
%K cyclic transition state
%X Chiral, nonracemic 1,3-diamines were prepared in a highly diastereoselective reduction of diaryl N-tert-butanesulfinylketimines. Correlation between facial selectivity of the reduction and E or Z geometry of the starting ketimines suggests involvement of a cyclic transition state for the reduction. The ortho-substituent controls the geometry of N-tert-butanesulfinylketimines in the solid state and provides additional stabilization of the cyclic transition state.
%I ACS Publications