期刊
TETRAHEDRON LETTERS
卷 53, 期 38, 页码 5148-5150出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.07.066
关键词
Chiral spirooxindolopyrrolizidines; Asymmetric 1,3-dipolar; Chiral auxiliaries; Azomethine ylide; Three-component reaction
资金
- Research Council of Shahid Beheshti University
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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