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Synthesis of 3-amino sugars of the daunosamine type through hetero-Diels-Alder reaction of enaminones

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
27
Issue
51
Identifiers
DOI: 10.1016/s0040-4039(00)85427-1
Disciplines
  • Physics

Abstract

Abstract The thermally induced hetero-Diels-Alder reaction of vinyl ethers 2a-d and N-acylenaminones 3a-h leads to the diastereomeric adducts 4a-h and 5a-h in 75–98% yield providing cis -compounds 4a-h as the main products. Isomerisation of 4a-f with Lewis acids gives the thermodynamically more stable 5a-f. Transformation of 4 and 5 by hydrogenation leads to 3-amino sugar glycosides.

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