Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of Enantiopure N-tert-Butanesulfinylketimines: Unusual Directing Effects of the ortho-Substituent

作者：Martjuga Marina; Shabashov Dmitry; Belyakov Sergey; Liepinsh Edvards; Suna Edgars^*

来源：Journal of Organic Chemistry, 2010, 75(7): 2357-2368.

DOI：10.1021/jo100173f

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.

• 出版日期2010-4-2