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

Subject Areas : International Journal of Bio-Inorganic Hybrid Nanomaterials

Received: 2013-09-24 Accepted : 2013-12-01 Published : 2013-10-01

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

Abstract :

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.