Journal
TETRAHEDRON LETTERS
Volume 53, Issue 38, Pages 5148-5150Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.07.066
Keywords
Chiral spirooxindolopyrrolizidines; Asymmetric 1,3-dipolar; Chiral auxiliaries; Azomethine ylide; Three-component reaction
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Funding
- Research Council of Shahid Beheshti University
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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. (C) 2012 Elsevier Ltd. All rights reserved.
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