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Original Articles

Thermal and Catalytic Diels-Alder Reactions Between (2E)-4, 5,6-Tri-O-acetyl-2,3-dideoxy-aldehydo-D-erythro -Hex-2-Enose and Cyclopentadiene

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Pages 1121-1134 | Received 13 Dec 1993, Accepted 12 Jul 1994, Published online: 24 Sep 2006

References

  • Carruthers , W. 1990 . “ Tetrahedron Organic Chemistry Series ” . In Cycloaddition Reactions in Organic Synthesis , vol. 8 , New York : Pergamon Press .
  • Giuliano , R. M. , ed. Cycloaddition Reactions in Carbohydrate Chemistry ACS Symp. Ser. pp. 494 Washington DC .
  • Román , E. , Hodgson , D. J. , Yokomori , Y. , Eliel , E. L. , Bueno Martínez , M. and Serrano , J. A. 1988 . Carbohydr. Res. , 180 : 263
  • Serrano , J. A. and Román , E. 1989 . J. Org. Chem. , 54 : 6114
  • Moreno , Ch. M. , Plumet , J. , Román , E. , Serrano , J. A. , Rodríguez , M. L. and Ruiz-Pérez , C. 1979 . Tetrahedron Lett. , 30 : 3179
  • Serrano , J. A. , Moreno , Ch. M. , Román , E. , Arjona , O. , Plumet , J. and Jiménez , J. 1991 . J. Chem. Soc., Perkin Trans. 1 , 3207
  • Serrano , J. A. , Cáceres , L. E. and Román , E. 1992 . J. Chem. Soc., Perkin Trans. 1 , 941
  • Horton , D. and Koh , D. 1993 . Tetrahedron Lett. , 34 : 2283 and references therein
  • Galán , E. R. , Chamizo , M. J. and Serrano , J. A. 1993 . Tetrahedron Lett. , 34 : 1811
  • Berson , J. A. and Ben-Efraim , D. A. 1959 . J. Am. Chem. Soc. , 81 : 4083
  • Takano , S. , Sugihara , T. , Samizu , K. and Ogasawara , K. 1988 . Heterocycles , 27 : 2103
  • González , F. , Lesage , S. and Perlin , A. S. 1975 . Carbohydr. Res. , 42 : 267
  • These ratios were determined from the 1H NMR spectra of the mixtures, by integration of the signals corresponding to a formyl proton from each sterereoisomer. Progress of the reactions (% react.) were also obtained from 1H NMR, taking into account the integral of formyl protons for the adducts and for the non-reacted α,β-unsaturated aldehyde
  • Bonnesen , P. V. , Puckett , C. L. , Honeychuck , R. V. and Hersh , W. H. 1989 . J. Am. Chem. Soc. , 111 : 6070
  • Fringuelli , F. , Pizzo , F. , Tatichi , A. and Wenkert , E. 1983 . J. Org. Chem. , 48 : 2802
  • Fleming , I. , Michael , J. P. , Overman , L. E. and Taylor , G. F. 1978 . Tetrahedron Lett. , 15 : 1313
  • Inukai , T. and Kojima , T. 1966 . J. Org. Chem. , 31 : 2032
  • Alder , K. , Stein , G. , Liebmann , M. and Rolland , E. 1934 . Ann. , 514 : 197
  • Kobuke , Y. , Fueno , T. and Furukawa , J. 1970 . J. Am. Chem. Soc. , 92 : 6541
  • Güner , O. F. , Ottenbrite , R. M. , Shillady , D. D. and Alston , P. V. 1988 . J. Org. Chem. , 53 : 5348
  • Smith , J. R. L. , Norman , R. O. C. and Stillings , M. R. 1978 . Tetrahedron , 34 : 1381
  • Batllori , R. , Font , J. , Monsalvatge , M. , Ortuño , R. M. and Sánchez-Ferrando , F. 1989 . Tetrahedron , 45 : 1833
  • Rideout , D. C. and Breslow , R. 1980 . J. Am. Chem. Soc. , 102 : 7816
  • Breslow , R. , Maitra , U. and Rideout , D. 1983 . Tetrahedron Lett. , 24 : 1901
  • Grieco , P. A. , Garner , P. and He , Z. 1983 . Tetrahedron Lett. , 24 : 1897
  • Horton , D. , Machinami , T. and Takagi , Y. 1983 . Carbohydr. Res. , 121 : 135
  • Kahn , S. D. and Hehre , W. J. 1987 . J. Am. Chem. Soc. , 109 : 663
  • Bhaté , P. and Horton , D. 1983 . Carbohydr. Res. , 122 : 189
  • Knapp , S. , Sankar Lal , G. and Sahai , D. 1986 . J. Org. Chem. , 51 : 380
  • Kreuzfel , H. J. and Döbler , Chr. 1981 . React. Kinet. Catal. Lett. , 16 : 229
  • Abraham , R. J. , Coppell , S. M. and Ramage , R. 1974 . Org. Magn. Reson. , 6 : 578
  • Blanc-Muesser , M. , Defaye , J. and Horton , D. 1980 . Carbohydr. Res. , 87 : 71
  • Vandevalle , M. , Eycken , J. V. d. , Oppolzer , W. and Vullioud , C. 1986 . Tetrahedron , 42 : 4035 See as example

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