Journal
TETRAHEDRON LETTERS
Volume 52, Issue 28, Pages 3610-3613Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.05.009
Keywords
Isatin; Magnesium iodide; Morita-Baylis-Hillman adduct; Spirocyclopropane-2-oxindole; Dimerization-spirocyclopropanation
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Funding
- Council of Scientific and Industrial Research (CSIR), New Delhi
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A novel magnesium iodide mediated unusual dimerization-spirocyclopropanation of bromo isomerised Morita-Baylis-Hillman adducts of isatin afforded highly functionalized 3-spirocyclopropane-2-oxindole derivatives as regioisomers in good combined yield. It has been observed that the regioselectivity is dependent on the nature of electron withdrawing group at the activated position. A plausible mechanism involving organomagnesium reagent has been proposed. (C) 2011 Elsevier Ltd. All rights reserved.
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