Enantioselective Hydrogenation of Allylphthalimides: An Efficient Method for the Synthesis of [beta]-Methyl Chiral AminesThis work was supported by the National Institutes of Health. We acknowledge the generous gift of Ru complexes from Heraeus Inc.
نویسندگان
چکیده
treatment of asthma. Compound B (NPS 1392) is a potent stereoselective antagonist of the NMDA receptor, which can be used for the control of ischemic strokes. To our knowledge, there has been no successful catalytic method to make such important functional groups. Although some stoichiometric asymmetric synthesis or resolution routes have been reported for constructing this class of chiral amines, the development of efficient and catalytic synthetic methods remains a significant challenge. Herein we report the first highly enantioselective catalytic asymmetric hydrogenation of disubstituted allylphthalimides to form chiral phthalimides, which act as precursors to the b-methyl chiral amines [Eq. (1)].
منابع مشابه
A Highly Enantioselective Brønsted Acid Catalyzed Cascade Reaction: Organocatalytic Transfer Hydrogenation of Quinolines and their Application in the Synthesis of AlkaloidsThe authors acknowledge Degussa AG for generous funding
The enantioselective hydrogenation of olefins, ketones, and imines still represents an important topic in organic synthesis and catalysis. Although many highly enantioselective processes based on chiral Rh, Ru, and Ir complexes have been reported, most of these catalysts failed to give satisfactory results in the asymmetric hydrogenation of aromatic and heteroaromatic compounds. Examples of eff...
متن کاملAn Efficient and One-pot Procedure for the Synthesis of Chiral Isoxazolidine via Catalytic Highly Enantioselective 1,3-dipolar cycloaddition
Synthesis of enantiomerically pure isoxazolidine via an asymmetric 1,3- dipolar cycloaddition reaction of nitrone with electron-deficient dipolarophile was described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendate bis(imine)–Cu(II)triflate complex as catalyst. The reaction mechanism is discussed on the basis of the assignment of t...
متن کاملPractical synthesis of enantiopure gamma-amino alcohols by rhodium-catalyzed asymmetric hydrogenation of beta-secondary-amino ketones.
Enantioselective hydrogenation of amino ketones catalyzed by Ru– or Rh–phosphine complexes provides an efficient method for the synthesis of enantiomerically active amino alcohols, a class of chiral compounds of great importance in pharmaceutical products. A recent challenging target inspired us to look for a practical solution for the enantioselective reduction of b-amino ketones with a second...
متن کاملEnantioselective Release Behavior of Ketoprofen Enantiomers from Alginate-metal Complexes, Monitored by Chiral HPLC
Alginate-metal complexes were prepared with divalent (Ca, Ba, Zn) and trivalent metals (Fe, Al) via congealing method in form of beads. Alginate mixed metals (Ca & Fe) complexes were also prepared by simultaneous and consecutive congealing. The studied beads were blank beads and racemic ketoprofen (KTP) loaded beads. Metal content was determined by atomic absorption spectroscopy and was 1.8% to...
متن کاملChiral Induction in Cycloaddition Reactions of Azomethine Ylides to Synthesis of New Enantiomerically Pure Spiro Oxindolopyrrolizidines
An efficient one-pot three-component procedure for the synthesis of new chiral spiro-oxindolopyrrolizidines with highly regio-, diastereo-, and enantioselective from 1,3-dipolar cycloaddition of azomethine ylides and optically pure active cinamoyl oxazolidinone are described. The process occurs at room temperature in aqueous ethanol as green solvent and in the absence of any bidentate chelating...
متن کامل