%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