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

Journal of Organic Chemistry 2010
Marina Martjuga, Dmitrijs Šabašovs, Sergejs Beļakovs, Edvards Liepiņš, Edgars Sūna

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.

Keywords
1,3-diamines, N-tert-butanesulfinylketimines
DOI
10.1021/jo100173f
Hyperlink
http://pubs.acs.org/doi/abs/10.1021/jo100173f

Martjuga, M., Šabašovs, D., Beļakovs, S., Liepiņš, E., Sūna, E. Asymmetric Synthesis of 1,3-Diamines by Diastereoselective Reduction of Enantiopure N-tert-Butanesulfinylketimines: Unusual Directing Effects of the Ortho-Substituent. Journal of Organic Chemistry, 2010, Vol. 75, No. 7, pp.2357-2368. ISSN 0022-3263. Available from: doi:10.1021/jo100173f

Publication language
English (en)