Remarkable change of the diastereoselection in the dye-sensitized ene hydroperoxidation of chiral alkenes by zeolite confinement.
[reaction: see text] The ene reaction of singlet oxygen with chiral trisubstituted alkenes bearing an alkyl and a phenyl group at the stereogenic center is erythro diastereoselective in solution and threo diastereoselective if carried out within zeolite Na-Y. The change of the diastereoselection trend by zeolite confinement is attributed to a synergism of steric effects and cation-pi interactions.
Stratakis
Manolis
M
Department of Chemistry, University of Crete, 71409 Iraklion, Greece.
Kalaitzakis
Dimitris
D
Stavroulakis
Dimitris
D
Kosmas
Giannis
G
Tsangarakis
Constantinos
C