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Synthesis of D-erythrose and D-threose derived nitrones and cycloadditions to styrene

✍ Scribed by Juraj Kubáň; Iva Blanáriková; L'ubor Fišera; Libuše Jarošková; Marion Fengler-Veith; Volker Jäger; Jozef Kožíšek; Otakar Humpa; Nad'a Prónayová; Vratislav Langer

Book ID
104209517
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
742 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

The new nitrones derived from cyclic acetals of D-erythrose (2a-c) and Dthreose (8) react with styrene to afford the corresponding 3,5-disubstituted diastereomeric isoxazolidines 3-6 and 9-12. The stereoselectivity was dependent on the steric hindrance of the nitrone. The major products 3a-c (55-58 %) and 9 (73 %) were found to have the C-3/C-4" erythro and C-31C-5 cis relative configuration by X-ray analysis. Its formation can be rationalized by less hindered endo attack of the Z-nitrone in an antiperiplanar manner with respect to the largest group of the cyclic acetal.

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