Tetrahedron Letters p. 5273 - 5276 (1985)
Update date:2022-08-04
Topics:
Tietze, Lutz F.
Voss, Edgar
Harms, Klaus
Sheldrick, George M.
N-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 phtalimide 11 does not react because of deconjugation of the electron accepting function in the α-position.
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