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Synlett 1991; 1991(4): 260-262
DOI: 10.1055/s-1991-20700
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Carbohydrates as Chiral Templates: Stereoselective Diels-Alder Synthesis with Dienes of Differing Reactivity

Wolfgang Stähle* , Horst Kunz
  • *Institut für Organische Chemie, Universität Mainz, Becher-Weg 18-20, D-6500 Mainz, Germany
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Publication Date:
07 March 2002 (online)

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With appropriate variation of the Lewis acidity and temperature, dienes of quite differing reactivity are transformed stereoselectively to either their (R)- or (S)-configurated Diels-Alder adducts using acrylates linked to O-3 of either dihydroglucal 1 (1,5-anhydro-2-deoxy- 4,6-di-O-pivaloyl-D-arabino-hexitol) or dihydrorhamnal 2 (1,5-anhydro-2,6-dideoxy-4-O-pivaloyl-L-arabino-hexitol), respectively, as the chiral templates.