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Investigation of the Enantioselectivity Observed in Epoxidation Reactions Catalysed by Bis‐Strapped Chiral Porphyrins Derived from L ‐Proline
Author(s) -
Boitrel Bernard,
BaveuxChambenoît Valérie,
Richard Philippe
Publication year - 2002
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/1099-0682(200207)2002:7<1666::aid-ejic1666>3.0.co;2-#
Subject(s) - chemistry , proline , chirality (physics) , stereochemistry , catalysis , enantioselective synthesis , medicinal chemistry , organic chemistry , amino acid , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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 D 2 ‐ or C 2 ‐symmetrical catalysts, for which the two sides are identically functionalised. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)