Abstract
A facile one-pot synthesis of carbohydrate derived spiro heterocycles via [3+2] cycloaddition reaction of azomethine ylides is described. A unique dipolarophile synthesized from d-glucose reacted with azomethine ylide generated in situ from secondary α-amino acids (sarcosine, proline, or pipecolinic acid) and 1,2-diketone (isatin/acenaphthoquinone)/indenoquinoxalinone to give their corresponding cycloadducts in good yield. The regio- and stereochemical outcome of the cycloaddition reaction is ascertained by X-ray crystallographic analysis.
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