Synthesis of new enantiomerically pure spirooxindolopyrrolizidines via a three-component asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides derived from isatin

Tetrahedron Letters

Volume 38 - Number 53

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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.