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

作者：Rao J Naga Siva; Raghunathan R^*

来源：Tetrahedron Letters, 2012, 53(7): 854-858.

DOI：10.1016/j.tetlet.2011.12.025

• 1,3-Dipolar cycloaddition
• Azomethine ylide
• Pyrrolidinyl-spirooxindoles
• alpha,beta-Unsaturated sugar lactones

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.

• 出版日期2012-2-15