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An efficient,one-pot,three-component procedure for the synthesis of chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition
Authors:Farbod Salahi  Mohammad Javad Taghizadeh  Hamid Arvinnezhad  Mehdi Moemeni  Khosrow Jadidi  Behrouz Notash
Affiliation:1. Department of Chemistry, Shahid Beheshti University, G.C. Tehran 1983963113, Iran;2. Department of Chemistry, Imam Hossein University, Tehran, Iran
Abstract:The catalytic, highly regio-, diastereo-, and enantioselective synthesis of a small library of chiral spirooxindolopyrrolizidines via a three-component 1,3-dipolar cycloaddition reaction of azomethine ylides, derived from isatin, with electron-deficient dipolarophiles, 3-(2-alkenoyl)-1,3-oxazolidin-2-ones, is described. A chiral copper(II) complex of cyclohexane-1,2-bis(arylmethyleneamine) catalyzed this process at room temperature. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts.
Keywords:Catalytic asymmetric multicomponent reaction   Asymmetric 1,3-dipolar cycloaddition   Cyclohexane-1,2-bis(arylmethyleneamine)   Azomethine ylide   Chiral spirooxindolopyrrolizidines
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