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Synthesis 2000; 2000(12): 1719-1726
DOI: 10.1055/s-2000-8214
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Enantioselective Diels-Alder Reaction with an α-Chloronitrose Dienophile Derived from 5-O-Acetyl-2,3-isopropylidenedioxy-d-ribose

Albert Defoin* , Muriel Joubert, Jean-Marc Heuchel, Christiane Strehler, Jacques Streith
  • *École Nationale Supérieure de Chimie de Mulhouse, Université de Haute-Alsace, 3, rue A. Werner, F-68093 Mulhouse Cédex, France; Fax +33 (0)3 89 33 68 75; E-mail: A.Defoin@univ-mulhouse.fr
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Publication Date:
31 December 2000 (online)

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Crystalline 5-O-acetyl-2,3-isopropylidenedioxy-d-ribonolactone oxime (8) was synthesised from d-ribose in 40% overall yield. The chloronitroso dienophile 3b was obtained from 8 by oxidation with t-BuOCl and underwent asymmetric Diels-Alder reaction with cyclic and acyclic dienes 10-13 to give crystalline adducts 14a-17a in good yield and excellent enantiomeric excess (93-99%).

asymmetric DielsAlder reaction - 1,2-oxazines - d-ribose derivatives - chloronitroso dienophiles - heterocycles