The high pressure mediated intramolecular diels-alder reaction of furans: Factors controlling cycloaddition with monoactivated dienophiles. |
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| Institution: | 1. Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford OX1 3QY U.K.;2. Department of Chemistry, University of Reading, Whiteknights, P.O. Box 224, Reading RG6 2AD U.K.;3. I.C.I. Pharmaceuticals, Mereside, Alderley Park, Macclesfield, SK10 4TG U.K.;4. Chemical Crystallography Laboratory, University of Oxford, Parks Road, Oxford OX1 3PD U.K.;1. Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan;2. Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan;1. Centro de Investigação em Química, Department of Chemistry and Biochemistry, Faculty of Science, University of Porto, Rua do Campo Alegre, 687, P-4169-007 Porto, Portugal;2. Instituto de Ciências Biomédicas Abel Salazar, ICBAS, University of Porto, Rua de Jorge Viterbo Ferreira, 228, P-4050-313 Porto, Portugal |
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| Abstract: | The Intramolecular Diels-Alder reactions of furans possessing a 2-alkyl substituent with a terminal α,β-unsaturated ketone have been surveyed. The consequences of varying the degree of substitution of the furan, the bridging chain length, and position of the activating group on the dienophile upon the ease and stereochemistry of cycloaddition are reported. |
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