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    Structural determination of coumarin derivatives. Diels-Alder adducts using 3-methylene-2,4-chromanedione as trapping agent

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    With a series of unsatured compounds, 3-methylene-2,4-chromanedione can behave as ambident heterodiene or as dienophile affording the hetero-Diels-Alder and Diels-Alder adducts, respectively. The structural analysis aimed at identifying the peculiar spectral parameters of these adducts, has been performed via multidimensional NMR experiments supported by Molecular Mechanics calculations

    The Chemistry of Coumarin Derivatives .6. Diels-alder Trapping of 3-methylene-2,4-chromandione - A New Entry To Substituted Pyrano[3,2-c]coumarins

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    3-Methylene-2,4-chromandione (1) can be generated from dicumarol or from paraformaldehyde and 4-hydroxycoumarin. 1 is a versatile substrate for cycloaddition reactions. Depending on the reaction partner, 1 can behave as an ambident heterodiene or as a dienophile. The reaction was investigated with a series of olefins and dienes, including several isoprenoids. Some generalizations could be drawn and rationalized in terms of HOMO-LUMO interactions. The reaction of 1 and certain asymmetrically substituted olefins gives pyrano[3,2-c]coumarins in a highly regio- and chemoselective way. As an application of this reaction to natural products chemistry, a concise (three steps) synthesis of the prenylated coumarin (+/-)-isoferprenin (35a) is reported

    A straightforward entry into enantiomerically enriched beta-amino-alpha-hydroxyphosphonic acid derivatives

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    The asymmetric aminohydroxylation (AA) reaction of beta-substituted vinylphosphonates under Sharpless protocol followed by hydrolysis afforded beta-amino-alpha-hydroxyphosphonic acids in moderate to good ee. (C) 1998 Elsevier Science Ltd. All rights reserved
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