Download PDF
Synlett 1996; 1996(3): 189-200
DOI: 10.1055/s-1996-5366
account
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Azasugar Syntheses and Multistep Cascade Rearrangements via Hetero Diels-Alder Cycloadditions with Nitroso Dienophiles

Jacques Streith* , Albert Defoin
  • *Ecole Nationale Supérieure de Chimie, Université de Haute-Alsace, 3, rue Alfred Werner, F-68093 MULHOUSE CEDEX, FRANCE, FAX: 33 89 59 98 59
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Hetero Diels-Alder (HDA) reactions with nitroso dienophiles R-N=0 are shown to represent the key step in the stereospecific total synthesis of azasugar derivatives. A series of amino-deoxysugars, both racemic and chiral, have been prepared from the primary cycloadducts of such HDA-reactions. Asymmetric induction during these cycloadditions were achieved either with chiral dienes, or with chiral nitroso dienophiles. In some instances the primary HDA cycloadducts underwent spontaneous cascading rearrangements to thermodynamically more stable entities. These rearrangements were triggered off by the breaking at r.t. of the weak N-O single bond.

hetero Diels-Alder - nitroso dienophiles - asymmetric induction - cascading rearrangements - azasugars