86457-67-2Relevant academic research and scientific papers
Catalytic Asymmetric Epoxidations with Chiral Iron Porphyrins
Groves, John T.,Myers, Richard S.
, p. 5791 - 5796 (2007/10/02)
Iron porphyrins have been modified to include optically active functionalities at the meso positions.Asymmetric epoxidations of prochiral olefins with these chiral iron porphyrins and iodosyl compounds have been investigated.Thus, 5α,10β,15α,20β-tetrakis(o-(R)-hydratropamidophenyl)porphyrin (H2T(α,β,α,β-Hyd)PP) and 5α,10β,15α,20β-tetrakis(ophenyl)porphyrin (H2T(α,β,α,β-Binap)PP) were synthesized by the condensation of optically active acid chlorides with 5α,10β,15α,20β-tetrakis(o-aminophenyl)porphyrin.Subsequent insertion of iron into H2T(α,β,α,β-Hyd)PP and H2T(α,β,α,β-Binap)PP gave FeT(α,β,α,β-Hyd)PPCl and FeT(α,β,α,β-Binap)PPCl, respectively.Emploing FeT(α,β,α,β-Hyd)PPCl iodosylbenzene, styrene was oxidized to (R)-(+)-styrene oxide in 31percent ee.Similarly, FeT(α,β,α,β-Binap)PPCl and iodosylmesitylene gave (R)-(+)-styrene oxide in 48percent ee.Various substituted styrenes and aliphatic olefins were epoxidized with enantiomeric excesses varying between 0percent for 1-methylcyclohexene oxide and 51percent for p-chlorostyrene oxide.
