ملخص
The salen μ-oxo complex of aluminum 1 catalyzes the asymmetric 1,4-addition of the novel ammonia equivalent 3,4,5,6-tetrafluorophthalimide to unsaturated ketones. All of the reagents are inexpensive and are readily available. The products are formed in up to 89% yield and up to 96% ee. The tetrafluorophthalimide group is removed under mild chemoselective conditions and in high yields to afford the free primary amines. Mechanistic studies suggest that the reaction occurs through a dual activation mechanism. A pre-equilibrium formation of a 1:1 complex between tetrafluorophthalimide and the catalyst is observed. The rate-determining step is the addition of tetrafluorophthalimide catalyst complex to the catalyst activated enone. These mechanistic studies provide important clues for the further development of catalytic asymmetric reactions. (Chemical Presented).
اللغة الأصلية | الإنجليزيّة |
---|---|
الصفحات (من إلى) | 336-342 |
عدد الصفحات | 7 |
دورية | ACS Catalysis |
مستوى الصوت | 5 |
رقم الإصدار | 1 |
المعرِّفات الرقمية للأشياء | |
حالة النشر | نُشِر - 2 يناير 2015 |
منشور خارجيًا | نعم |