Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines
نویسندگان
چکیده
A rapid and simple procedure was devised for the synthesis of multifunctionalized cyclic β-amino esters and γ-amino alcohols via the 1,3-dipolar cycloaddition of nitrile oxides to β-aminocyclopentenecarboxylates. The opening of the isoxazoline reductive ring to the corresponding highly functionalized 2-aminocyclopentanecarboxylates occurred stereoselectively with good yields.
منابع مشابه
One-pot synthesis of highly regioselective β-azido alcohols catalyzed by Brønsted acidic ionic liquids
In this protocol, 3-(2-carboxybenzoyl)-1-methyl-1H-imidazol-3-ium chloride [Cbmim]Cl and sulfonic acid functionalized pyridinium chloride [pyridine-SO3H]Cl as a new, reusable, and green Brønsted acidic ionic liquid (BAIL) catalyst were synthesized and successfully used for the one-pot ring opening of epoxide with sodium azide (NaN3) in water at room temperature. Epoxides under ring-opening easi...
متن کاملTrichloroacetic Acid as an Efficient Catalyst for One-pot Synthesis of Highly Functionalized Piperidines via multi-component Reaction
Trichloroacetic Acid (TCA) was used as an efficient catalyst for the synthesis of highly functionalized piperidines via a one-pot five-component reaction of aromatic amines, aromatic aldehydes and β-keto esters in MeOH at room temperature. The remarkable advantages offered by this method are good yields, simple procedure, short reaction times, no need to column chromatography and an easy wo...
متن کاملOne pot, Five-component Synthesis of Functionalized Piperidines Using Zn(OAc)2.2H2O as a Highly Efficient Catalyst
A convenient synthetic route for the synthesis of biologically active functionalized piperidines usingZn(OAc)2.2H2O as a highly efficient catalyst via five-component reaction of aromatic aldehydes,anilines and β-ketoesters at ambient temperature has studied. Mild reaction conditions, simplicity ofoperation and work-up procedures with no necessity of chromatographic purification steps, theavaila...
متن کاملB-podands as efficient catalysts for the ring opening of epoxides in water: A versatile and atom economical method for the synthesis of vicinal azidoalcohols
For the first time B-podands have been studied as an efficient and powerful catalysts in the ring opening of epoxides with azide anion in water. The reaction afforded the corresponding 1,2-azidoalcohols with high regioselectivity under mild reaction conditions and in a highly atom economic fashion.
متن کاملB-podands as efficient catalysts for the ring opening of epoxides in water: A versatile and atom economical method for the synthesis of vicinal azidoalcohols
For the first time B-podands have been studied as an efficient and powerful catalysts in the ring opening of epoxides with azide anion in water. The reaction afforded the corresponding 1,2-azidoalcohols with high regioselectivity under mild reaction conditions and in a highly atom economic fashion.
متن کامل