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Title
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Synthesis of new enantiomerically pure spirooxindolopyrrolizidines via a three-component asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides derived from isatin
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Type
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JournalPaper
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Keywords
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Chiral spirooxindolopyrrolizidines, Asymmetric 1,3-dipolar, Chiral auxiliaries, Azomethine ylide, Three-component reaction
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Abstract
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An efficient, one-pot, three-component procedure for the synthesis of a small library of new chiral spirooxindolopyrrolizidines with high regio-, diastereo-, and enantioselectivity, from the 1,3-dipolar cycloaddition of azomethine ylides and optically active cinnamoyl oxazolidinone is described. The process occurs at room temperature in aqueous ethanol as a green solvent and in the absence of any Lewis acids. The oxazolidinone chiral auxiliary is removed in a non-destructive manner. The reaction mechanism is discussed on the basis of the assignment of the absolute configuration of the cycloadducts, and on theoretical calculations.
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Researchers
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Behrouz Notash (Not In First Six Researchers), Abdollah Javidan (Fifth Researcher), Khosrow Jadidi (Fourth Researcher), Saadi Samadi (Third Researcher), Hamid Arvinnezhad (Second Researcher), Mohammad Javad Taghizadeh (First Researcher)
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