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Stereoselective cycloaddition of 1-glucosyl-1,3-butadienes with tert-butyl 2H-azirine-3-carboxylate, glyoxylates and imines

✍ Scribed by M.José Alves; I.G. Almeida; A. Gil Fortes; A.P. Freitas

Book ID
104254283
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
444 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Glucosyl dienes 1 have been reacted with the achiral 2H-azirine 4 and with glyoxylates, forming fused structures of type 5 and disaccharide-like compounds 7 with good to excellent selectivity. Glucosyl dienes 1 participated as dienophiles in reactions with Schiff bases derived from anilines forming isoquinolines 10 and 11. The diastereoselectivity of this reaction is poor.

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