Asymmetric Epoxidation of Unfunctionalized Alkenes with Ammonium and Phosphonium Monopersulfates Catalyzed by Chiral Mn(III)–Salen Complexes
Publication type: Journal Article
Publication date: 2000-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Simple cis-disubstituted and trisubstituted alkenes were enantioselectively epoxidized in mild conditions using various Mn(III)–salen complexes as catalysts and quaternary ammonium and phosphonium monopersulfates (Bu4NHSO5, Ph4PHSO5) as oxidants together with amine N-oxides as additives. The effect of the catalyst structure on the stereochemical outcome of the epoxidation reactions was studied. Generally, the 1,2-diphenylethylenediamine-derived complexes were found to give higher asymmetric induction compared to their 1,2-diaminocyclohexane-derived counterparts. Particularly high yields of epoxides (up to 98%) and good enantiomeric excesses (ee up to 93%) were obtained in the epoxidation of 2,2-dialkylchromenes and trisubstituted alkenes.
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GOST
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Pietikäinen P. Asymmetric Epoxidation of Unfunctionalized Alkenes with Ammonium and Phosphonium Monopersulfates Catalyzed by Chiral Mn(III)–Salen Complexes // Tetrahedron. 2000. Vol. 56. No. 3. pp. 417-424.
GOST all authors (up to 50)
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Pietikäinen P. Asymmetric Epoxidation of Unfunctionalized Alkenes with Ammonium and Phosphonium Monopersulfates Catalyzed by Chiral Mn(III)–Salen Complexes // Tetrahedron. 2000. Vol. 56. No. 3. pp. 417-424.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/S0040-4020(99)01008-X
UR - https://doi.org/10.1016/S0040-4020(99)01008-X
TI - Asymmetric Epoxidation of Unfunctionalized Alkenes with Ammonium and Phosphonium Monopersulfates Catalyzed by Chiral Mn(III)–Salen Complexes
T2 - Tetrahedron
AU - Pietikäinen, Pekka
PY - 2000
DA - 2000/01/01
PB - Elsevier
SP - 417-424
IS - 3
VL - 56
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
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@article{2000_Pietikäinen,
author = {Pekka Pietikäinen},
title = {Asymmetric Epoxidation of Unfunctionalized Alkenes with Ammonium and Phosphonium Monopersulfates Catalyzed by Chiral Mn(III)–Salen Complexes},
journal = {Tetrahedron},
year = {2000},
volume = {56},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/S0040-4020(99)01008-X},
number = {3},
pages = {417--424},
doi = {10.1016/S0040-4020(99)01008-X}
}
Cite this
MLA
Copy
Pietikäinen, Pekka. “Asymmetric Epoxidation of Unfunctionalized Alkenes with Ammonium and Phosphonium Monopersulfates Catalyzed by Chiral Mn(III)–Salen Complexes.” Tetrahedron, vol. 56, no. 3, Jan. 2000, pp. 417-424. https://doi.org/10.1016/S0040-4020(99)01008-X.