Facile construction of three contiguous stereogenic centers via dynamic kinetic resolution in asymmetric transfer hydrogenation of quinolines.
نویسندگان
چکیده
An efficient and facile route to chiral tetrahydroquinolines with three contiguous stereogenic centers via a dynamic kinetic resolution process has been successfully developed by using chiral phosphoric acid as catalyst and Hantzsch ester as the hydrogen source with up to 89% ee.
منابع مشابه
Palladium-catalyzed asymmetric hydrogenation of 3-phthalimido substituted quinolines.
Homogeneous Pd-catalyzed asymmetric hydrogenation of 3-phthalimido substituted quinolines was successfully developed, providing facile access to chiral substituted tetrahydroquinolines bearing two contiguous stereogenic centers with up to 90% ee.
متن کاملAsymmetric hydrogenation of α,α'-disubstituted cycloketones through dynamic kinetic resolution: an efficient construction of chiral diols with three contiguous stereocenters.
Chiral diols with three contiguous stereocenters were synthesized by a highly enantioselective ruthenium-catalyzed asymmetric hydrogenation of racemic α,α'-disubstituted cycloketones involving dynamic kinetic resolution. This new catalytic asymmetric method provides a concise route to the alkaloid (+)-γ-lycorane.
متن کاملDynamic kinetic resolution in the stereoselective synthesis of 4,5-diaryl cyclic sulfamidates by using chiral rhodium-catalyzed asymmetric transfer hydrogenation.
The dynamic kinetic resolution of 4,5-diaryl cyclic sulfamidate imines was achieved via asymmetric transfer hydrogenation using a HCO(2)H/Et(3)N mixture as the hydrogen source and chiral Rh catalysts (R,R)- or (S,S)-RhCl(TsDPEN)Cp* affording the corresponding cyclic sulfamidates in good yields with up to >20 : 1 dr and up to >99% ee.
متن کاملAsymmetric transfer hydrogenation of 3-nitroquinolines: facile access to cyclic nitro compounds with two contiguous stereocenters.
Hi, neighbor! The first organocatalyzed asymmetric transfer hydrogenation of aromatic nitro compounds was successfully developed with up to 99 % ee. The new methodology provides a direct and facile access to enantiopure cyclic nitro compounds with two contiguous stereocenters.
متن کاملPalladium-catalyzed asymmetric hydrogenolysis of N-sulfonyl aminoalcohols via achiral enesulfonamide intermediates.
Hydrogenolysis is an important synthetic method in organic chemistry, and has been widely applied in industrial processes, natural product synthesis, and the removal of waste materials. In practice, most hydrogenolysis reactions have been used for the synthesis of racemic or achiral compounds. Very few studies on asymmetric homogeneous hydrogenolysis have been reported. The first example, repor...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 50 83 شماره
صفحات -
تاریخ انتشار 2014