Journal
TETRAHEDRON LETTERS
Volume 53, Issue 7, Pages 854-858Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.12.025
Keywords
1,3-Dipolar cycloaddition; Azomethine ylide; Pyrrolidinyl-spirooxindoles; alpha,beta-Unsaturated sugar lactones
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Funding
- Council of Scientific and Industrial Research (CSIR), New Delhi, India
- DST, New Delhi [SR/S1/OC-51/2008]
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Synthesis of pyrrolidinyl-spirooxindoles fused to sugar lactone has been achieved by a one pot three component 1,3-dipolar cycloaddition (1,3-DC) reaction. A unique dipolarophile (alpha,beta-unsaturated lactone) derived from D-glucose/D-galactose reacted with azomethine ylide generated in situ from isatin/N-substituted isatin and secondary amino acids (sarcosine/proline/piperidine-2-carboxylic acid) to give the corresponding cycloadducts in good yield. The cycloaddition was found to be highly regio- and diastereoselective. (C) 2011 Elsevier Ltd. All rights reserved.
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