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Volumn 13, Issue 17, 2007, Pages 4849-4858

Synthesis of metal-(pentadentate-salen) complexes: Asymmetric epoxidation with aqueous hydrogen peroxide and asymmetric cyclopropanation (salenH 2: N,N′-bis(salicylidene)ethylene-1,2-diamine)

Author keywords

Asymmetric catalysis; Cyclopropanation; Epoxidation; Green chemistry; Salen ligands

Indexed keywords

APICAL LIGANDS; ASYMMETRIC CATALYSIS; GREEN CHEMISTRY; SALEN LIGANDS;

EID: 34250309655     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601420     Document Type: Article
Times cited : (55)

References (64)
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    • For recent reports on asymmetric epoxidation using aqueous hydrogen peroxide as a stoichiometric oxidant, see: a M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991;
    • For recent reports on asymmetric epoxidation using aqueous hydrogen peroxide as a stoichiometric oxidant, see: a) M. B. Francis, E. N. Jacobsen, Angew. Chem. 1999, 111, 987-991;
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    • Although P-450 possesses a thiol group as the apical ligand, Watanabe et al. have reported that a myoglobin mutant that has an imidazole group as the apical ligand shows comparable activity to P-450, and they have proposed that an intermediary hydroperoxo species is converted to the corresponding oxo species due to a synergis tic push-pull effect of the apical imidazole and distal histidine groups see ref, 10g
    • Although P-450 possesses a thiol group as the apical ligand, Watanabe et al. have reported that a myoglobin mutant that has an imidazole group as the apical ligand shows comparable activity to P-450, and they have proposed that an intermediary hydroperoxo species is converted to the corresponding oxo species due to a synergis tic push-pull effect of the apical imidazole and distal histidine groups (see ref. [10g]).
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    • For a review on asymmetric epoxidation using [Mn(salen)] complexes as catalysts in the presence of oxidants other than hydrogen peroxide, see: a) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214;
    • For a review on asymmetric epoxidation using [Mn(salen)] complexes as catalysts in the presence of oxidants other than hydrogen peroxide, see: a) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189-214;
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    • A part of this study has been communicated : H. Shitama, T. Katsuki, Tetrahedron Lett. 2006, 47, 3203-3207.
    • A part of this study has been communicated : H. Shitama, T. Katsuki, Tetrahedron Lett. 2006, 47, 3203-3207.
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    • The reaction in AcOEt was also slow and gave the corresponding epoxide of 95% ee in 9% yield after 24 h. The reaction in THF was sluggish.
    • The reaction in AcOEt was also slow and gave the corresponding epoxide of 95% ee in 9% yield after 24 h. The reaction in THF was sluggish.


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