An expedient diastereoselective synthesis of pyrrolidinyl spirooxindoles fused to sugar lactone via [3+2] cycloaddition of azomethine ylides

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 (α,β-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.

Figure optionsDownload as PowerPoint slide