Efficient construction of highly functionalized endo′-selective spiro[pyrrolidin-2,3′-oxindoles] via a regioselective 1,3-dipolar cycloaddition reaction between 3-amino oxindoles as azomethine ylide precursors and nitroalkenes |
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Authors: | Hongbao Sun Xiaoyan Wang Yi chen Liang Ouyang Jie Liu Yiwen Zhang |
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Institution: | 1. State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, China;2. Analytical & Testing Center, Sichuan University, Chengdu 610064, China |
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Abstract: | An efficient synthesis of novel endo′-selective spiropyrrolidin-2,3′-oxindoles] has been achieved via a three component regioselective 1,3-dipolar cycloaddition reaction. The azomethine ylides generated in situ from 3-amino oxindoles and aldehydes reacted with the nitroalkenes to furnish novel pyrrolidine–spirooxindole derivatives bearing one spiro quaternary center and multiple chiral centers in moderate to high yields (up to 99%) with high diastereoselectivities (up to 99:1). The structure and relative stereochemistry of cycloadducts were confirmed by NMR spectra and single crystal X-ray diffraction. The possible mechanism was proposed and the cycloaddition proceeded via endo′-transition state. |
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Keywords: | 1 3-Dipolar cycloaddition 3-Amino oxindole Pyrrolidine&ndash spirooxindole Nitroalkene Regioselectivity |
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