Three-Component Procedure for the Synthesis Chiral Spirooxindolopyrrolizidines via Catalytic Highly Enantioselective 1,3-Dipolar Cycloaddition of Azomethineylides and 3-(2-Alkenoyl)-1,3-Oxazolidin-2-ones

International Journal of Bio-Inorganic Hybrid Nanomaterials

مقاله 6، دوره 2، شماره 4، دی 2013، صفحه 503-510   

نوع مقاله: Research Paper

چکیده

The catalytic highly regio-, diastereo-, and enantioselective synthesis of a small library of spiropyrrolizidineoxindolesvia a four-component 1,3-dipolar cycloaddition reactionof azomethineylides, derived from isatin, with electron-deficient dipolarophilewas described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the presence of a bidendatebis(imine)–Cu(II)triflate complex as catalyst.The reaction mechanism is discussedon the basis of the assignment of the absolute configuration of the cycloadducts.

کلیدواژه‌ها

Chiral spiro-oxindolopyrrolizidines؛ Asymmetric 1,3-dipolar؛ Chiral auxiliaries؛ Azomethineylide؛ Three-component reaction؛ Proline؛ Sarcosine