209863-36-5Relevant academic research and scientific papers
Diels-Alder reactions of (R(s))-3-[(1S)-isoborneol-10-sulfinyl]- 1- methoxybuta-1,3-dienes with electron-deficient carbodienophiles. The effects of Lewis acid catalysis
Aversa, Maria C.,Barattucci, Anna,Bonaccorsi, Paola,Giannetto, Placido,Panzalorto, Manuela,Rizzo, Simona
, p. 1577 - 1587 (2007/10/03)
Uncatalyzed cycloadditions of (R(S),E)-1 and (R(S),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.
