An efficient,one-pot,three-component procedure for the synthesis of chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition |
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| Authors: | Farbod Salahi Mohammad Javad Taghizadeh Hamid Arvinnezhad Mehdi Moemeni Khosrow Jadidi Behrouz Notash |
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| Institution: | 1. Department of Chemistry, Shahid Beheshti University, G.C. Tehran 1983963113, Iran;2. Department of Chemistry, Imam Hossein University, Tehran, Iran |
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| 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. |
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| Keywords: | Catalytic asymmetric multicomponent reaction Asymmetric 1 3-dipolar cycloaddition Cyclohexane-1 2-bis(arylmethyleneamine) Azomethine ylide Chiral spirooxindolopyrrolizidines |
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