Rhodium(II) catalyzed highly diastereoselective synthesis of conformationally restricted dispiro[1,3-dioxolane]bisoxindoles |
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Authors: | Sengodagounder Muthusamy Rajagopal Ramkumar |
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Institution: | School of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, India |
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Abstract: | Synthesis of conformationally restricted dispiro- and bis-dispiro-1,3-dioxolanes via three-component reaction of diazoamides, ketoamides/diketones, and aromatic/heteroaromatic aldehydes in the presence of rhodium(II) acetate dimer catalyst at room temperature involving carbonyl ylides is demonstrated with diastereoselectivity. Synthesis of macrocyclic dispiro-1,3-dioxolanes via intramolecular carbonyl ylide is also delineated in high yield. The conformationally restricted symmetrical as well as unsymmetrical dispiro-1,3-dioxolanes were obtained under mild conditions in a highly diastereo- and regioselective manner. |
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Keywords: | Carbonyl ylides Dispirodioxolanes Diastereoselectivity Rhodium(II) acetate |
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