title: Asymmetric synthesis of 1,3-diamines by diastereoselective reduction of enantiopure N-tert-butanesulfinylketimines: unusual directing effects of the ortho-substituent.
abstract: 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.
authors.affiliation: Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, Latvia.
authors.forename: Marina
authors.initials: M
authors.lastname: Martjuga
authors.forename: Dmitry
authors.initials: D
authors.lastname: Shabashov
authors.forename: Sergey
authors.initials: S
authors.lastname: Belyakov
authors.forename: Edvards
authors.initials: E
authors.lastname: Liepinsh
authors.forename: Edgars
authors.initials: E
authors.lastname: Suna