TY - JOUR
T1 - Catalytic asymmetric epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes
AU - Irie, Ryo
AU - Noda, Keiko
AU - Ito, Yoshio
AU - Matsumoto, Naohide
AU - Katsuki, Tsutomu
N1 - Funding Information:
Acknowledgement: Financial supportb y the Grant-in-Aid for Scientific Researchi n priority Areas (02231222f)r om the Ministry of Education,S cience,a nd Culture,J apani s greatlya cknowledged.Support from Ono Pharmaceutical Company is also acknowledged. The authors are grateful to Professor Hisashi Okawa of this Department for his helpful discussions.
PY - 1991
Y1 - 1991
N2 - Several kinds of chiral (salen)manganese(III) complexes (2 and 3) having chiral salicylaldehyde and chiral ethylenediamine moieties were prepared and used for catalytic asymmetric epoxidation of unfunctionalized olefins with iodosobenzene as a terminal oxidant. Catalysts 2 and 3 were found to show the characteristic substrate specificity for the enantiofacial selection of olefins, respectively. Furthermore, the addition of donor ligands such as pyridine N-oxide or 2-methylimidazole to the epoxidation reaction system was found to alter the enantioselectivity. As a result, the highest enantioselectivity for nonenzaymatic catalytic epoxidation was achieved for (E)-1-phenylpropene (56% ee, with 2c in the presence of 2-methylimidazole), (E)-stilbene (48% ee, with 3a), and dihydronaphthalene (83% ee, with 3a in the presence of pyridine N-oxide).
AB - Several kinds of chiral (salen)manganese(III) complexes (2 and 3) having chiral salicylaldehyde and chiral ethylenediamine moieties were prepared and used for catalytic asymmetric epoxidation of unfunctionalized olefins with iodosobenzene as a terminal oxidant. Catalysts 2 and 3 were found to show the characteristic substrate specificity for the enantiofacial selection of olefins, respectively. Furthermore, the addition of donor ligands such as pyridine N-oxide or 2-methylimidazole to the epoxidation reaction system was found to alter the enantioselectivity. As a result, the highest enantioselectivity for nonenzaymatic catalytic epoxidation was achieved for (E)-1-phenylpropene (56% ee, with 2c in the presence of 2-methylimidazole), (E)-stilbene (48% ee, with 3a), and dihydronaphthalene (83% ee, with 3a in the presence of pyridine N-oxide).
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U2 - 10.1016/S0957-4166(00)86102-9
DO - 10.1016/S0957-4166(00)86102-9
M3 - Article
AN - SCOPUS:0025862121
SN - 0957-4166
VL - 2
SP - 481
EP - 494
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 7
ER -