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Get Free AccessN-acyl-enaminecarbaldehydes 6a - g with an electron accepting group in the α- position react in a hetero-Diels-Alder cycloaddition with enolethers 7a - g to 4-amino- dihydropyrans 8a - g, 9a - g and 10a - g. This reaction represents a convenient entry to branched aminosugars of the garosamine-type. The rate of the cycloaddition depends strongly on the N-acyl group in 6. However, the phthalimide 11 does not react because of deconjugation of the electron accepting function in the α-opposition.
Lutz F. Tietze, Edgar Voβ, Klaus Harms, In Memory: G.M. Sheldrick (1942–2025) (1985). Hetero-diels-alder reaction of enaminecarbaldehydes an entry to branched aminosugars. Tetrahedron Letters, 26(43), pp. 5273-5276, DOI: 10.1016/s0040-4039(00)95013-5.
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Type
Article
Year
1985
Authors
4
Datasets
0
Total Files
0
Language
English
Journal
Tetrahedron Letters
DOI
10.1016/s0040-4039(00)95013-5
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