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.
Atslēgas vārdi
1,3-diamines, N-tert-butanesulfinylketimines
DOI
10.1021/jo100173f
Hipersaite
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, 2357.-2368.lpp. ISSN 0022-3263. Pieejams: doi:10.1021/jo100173f
Publikācijas valoda
English (en)