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Chiral porphyrin imine manganese complex as catalyst for asymmetric epoxidation of styrene derivatives
Author(s) -
Ananthi Nallamuthu,
Enoch I.V. Muthu Vijayan
Publication year - 2019
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23043
Subject(s) - chemistry , styrene , imine , porphyrin , catalysis , asymmetric induction , trifluoroacetic acid , manganese , ligand (biochemistry) , chiral ligand , yield (engineering) , organic chemistry , polymer chemistry , medicinal chemistry , enantioselective synthesis , copolymer , biochemistry , polymer , receptor , materials science , metallurgy
New chiral porphyrin imine was synthesized from ( S )‐3‐benzyl‐2‐methyl‐4‐phenylbutanal according to dipyrromethane method using trifluoroacetic acid, BF 3 etherate, and p ‐chloranil. Manganese complex of this chiral porphyrin imine ligand was used as catalyst in the asymmetric epoxidation of styrene derivatives possessing different substituents. Styrene derivatives possessing electron withdrawing groups gave the corresponding chiral epoxides in high yield up to 98% and ee up to 99%. The mechanism for the catalytic asymmetric epoxidation was also discussed based on transfer of oxygen.