Synthetic and Mechanistic Study of the Catalytic Enantioselective Preparation of Primary β-Amino Ketones from Enones and a Fluorinated Gabriel Reagent

Shlomit Avidan-Shlomovich, Harisadhan Ghosh, Alex M. Szpilman

نتاج البحث: نشر في مجلةمقالةمراجعة النظراء

13 اقتباسات (Scopus)

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 الأصليةالإنجليزيّة
الصفحات (من إلى)336-342
عدد الصفحات7
دوريةACS Catalysis
مستوى الصوت5
رقم الإصدار1
المعرِّفات الرقمية للأشياء
حالة النشرنُشِر - 2 يناير 2015
منشور خارجيًانعم

بصمة

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