6533b82dfe1ef96bd12911dc

RESEARCH PRODUCT

Investigation of the Enantioselectivity Observed in Epoxidation Reactions Catalysed by Bis‐Strapped Chiral Porphyrins Derived from L ‐Proline

Valérie Baveux-chambenoîtPhilippe RichardBernard Boitrel

subject

Inorganic ChemistrySteric effectschemistry.chemical_compoundchemistryOrganic chemistryProlineEnantiomerMedicinal chemistryPorphyrinCatalysis

description

The enantiomeric excesses obtained during the epoxidation reactions of p-chlorostyrene or 1,2-dihydronaphthalene catalysed by two different series of chiral porphyrins are reported. An attempt is made to correlate the enantioselectivity with the steric hindrance generated by the straps of these catalysts. It is shown that this steric hindrance is influenced by the nature of the strap and that it can be approximated. Additionally, the same strap is tethered in two different fashions on each side of the porphyrin, leading to either D2- or C2-symmetrical catalysts, for which the two sides are identically functionalised.

https://doi.org/10.1002/1099-0682(200207)2002:7<1666::aid-ejic1666>3.0.co;2-#