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The Diels-Alder cycloaddition reaction of some substituted furans and E-1,2-bis(phenylsulfonyl)ethylene

✍ Scribed by Odón Arjona; Fátima Iradier; Rosario M. Mañas; Joaquín Plumet; Xavier Grabuleda; Carlos Jaime

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
855 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

The Diels-Alder cycloaddition between several 2-, and 3-substituted furans and E-i,2bis(phenylsulfonyl)ethylene have been carried out in high yields. Stereoselectivity observed in the case of 2-sustimted furans has been explained by means of the MM3-transition state model. The model had to be refined for 2-methoxyfuran due to the asymmetry induced over the transition state geometry by the electron-donating methoxyl group. Selectivity in 2-substituted furans arose by interactions between the 2substituent and the sulfonyi groups (steric repulsion with the cis-sulfonyl or long-range favourable interactions with the trans-sulfonyl).

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