Diels–Alder reactions of ( RS)-3-[(1 S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-dienes with electron-deficient carbodienophiles. The effects of Lewis acid catalysis

Uncatalyzed cycloadditions of ( R S,E)- 1 and ( R S,Z)-3-[(1 S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-diene 2 with maleimide and N-phenylmaleimide occurred with complete endo and very high facial diastereoselectivities. The effects of Lewis acid catalysis on these Diels–Alder reactions have been...

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Published inTetrahedron: asymmetry Vol. 9; no. 9; pp. 1577 - 1587
Main Authors Aversa, Maria C., Barattucci, Anna, Bonaccorsi, Paola, Giannetto, Placido, Panzalorto, Manuela, Rizzo, Simona
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.05.1998
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
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Summary:Uncatalyzed cycloadditions of ( R S,E)- 1 and ( R S,Z)-3-[(1 S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-diene 2 with maleimide and N-phenylmaleimide occurred with complete endo and very high facial diastereoselectivities. The effects of Lewis acid catalysis on these Diels–Alder reactions have been evaluated. LiClO 4 catalyzed cycloaddition of 1 with dimethyl maleate gave cyclohexene 13 as the unique product with complete control of endo and π-facial diastereoselectivities exerted by the sulfinyl group. A significant improvement in diastereoselectivity was also observed in the LiClO 4 catalyzed cycloaddition of 1 with dimethyl fumarate.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(98)00138-4