36271-03-1Relevant academic research and scientific papers
Asymmetric synthesis of 1,3-diamines by diastereoselective reduction of enantiopure n-tert-butanesulfinylketimines: unusual directing effects of the ortho-substituent
Martjuga, Marina,Shabashov, Dmitry,Belyakov, Sergey,Liepinsh, Edvards,Suna, Edgars
supporting information; experimental part, p. 2357 - 2368 (2010/07/02)
(Figure Presented) 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.
