Diels–Alder reactions of (RS)-3-[(1S)-isoborneol-10-sulfinyl]-1-methoxybuta-1,3-dienes with electron-deficient carbodienophiles. The effects of Lewis acid catalysis
1998; Elsevier BV; Volume: 9; Issue: 9 Linguagem: Inglês
10.1016/s0957-4166(98)00138-4
ISSN1362-511X
AutoresMaria C. Aversa, Anna Barattucci, Paola Bonaccorsi, Placido Giannetto, M. Panzalorto, Simona Rizzo,
Tópico(s)Chemical synthesis and alkaloids
ResumoAbstract Uncatalyzed cycloadditions of (RS,E)-1 and (RS,Z)-3-[(1S)-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. LiClO4 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 LiClO4 catalyzed cycloaddition of 1 with dimethyl fumarate.
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