Multinuclear NMR study of the reactive intermediates in enantioselective epoxidations of allylic alcohols catalyzed by a vanadium complex derived from a planar-chiral hydroxamic acid
Тип публикации: Journal Article
Дата публикации: 2003-01-15
scimago Q2
wos Q3
БС1
SJR: 0.493
CiteScore: 5
Impact factor: 2.5
ISSN: 11440546, 13699261
Materials Chemistry
General Chemistry
Catalysis
Краткое описание
Structure and reactivity of vanadium(V) complexes formed in situ in the catalytic system VO(Oalkyl)3/hydroxamic acid/tert-butylhydroperoxide (TBHP) have been examined by means of 51V, 13C and 17O NMR spectroscopy. For the first time, reactive vanadium(V) alkylperoxo intermediates in vanadium/hydroxamic acid epoxidations were observed and spectroscopically characterized. With a planar-chiral [2.2]paracyclophane-derived hydroxamate as ligand two diastereomeric alkylperoxo vanadium(V) complexes were formed in a 3∶1 ratio. They differ in the relative positioning of the VO group and the planar-chiral aromatic part. Upon addition of geraniol as substrate, these complexes disappear in a parallel manner, and geraniol epoxide is formed. Probably, the existence of these two diastereomeric complexes and their comparable reactivity account for the observed enantioselectivity level (≤71% ee) and hence sets a fundamental limitation for the use of such ligands in this asymmetric catalysis.
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Bryliakov K. P. et al. Multinuclear NMR study of the reactive intermediates in enantioselective epoxidations of allylic alcohols catalyzed by a vanadium complex derived from a planar-chiral hydroxamic acid // New Journal of Chemistry. 2003. Vol. 27. No. 3. pp. 609-614.
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Bryliakov K. P., Talsi E. P., Kühn T., Bolm C. Multinuclear NMR study of the reactive intermediates in enantioselective epoxidations of allylic alcohols catalyzed by a vanadium complex derived from a planar-chiral hydroxamic acid // New Journal of Chemistry. 2003. Vol. 27. No. 3. pp. 609-614.
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TY - JOUR
DO - 10.1039/b208748k
UR - https://doi.org/10.1039/b208748k
TI - Multinuclear NMR study of the reactive intermediates in enantioselective epoxidations of allylic alcohols catalyzed by a vanadium complex derived from a planar-chiral hydroxamic acid
T2 - New Journal of Chemistry
AU - Bryliakov, Konstantin P.
AU - Talsi, Evgenii P.
AU - Kühn, Toralf
AU - Bolm, Carsten
PY - 2003
DA - 2003/01/15
PB - Royal Society of Chemistry (RSC)
SP - 609-614
IS - 3
VL - 27
SN - 1144-0546
SN - 1369-9261
ER -
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@article{2003_Bryliakov,
author = {Konstantin P. Bryliakov and Evgenii P. Talsi and Toralf Kühn and Carsten Bolm},
title = {Multinuclear NMR study of the reactive intermediates in enantioselective epoxidations of allylic alcohols catalyzed by a vanadium complex derived from a planar-chiral hydroxamic acid},
journal = {New Journal of Chemistry},
year = {2003},
volume = {27},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://doi.org/10.1039/b208748k},
number = {3},
pages = {609--614},
doi = {10.1039/b208748k}
}
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Bryliakov, Konstantin P., et al. “Multinuclear NMR study of the reactive intermediates in enantioselective epoxidations of allylic alcohols catalyzed by a vanadium complex derived from a planar-chiral hydroxamic acid.” New Journal of Chemistry, vol. 27, no. 3, Jan. 2003, pp. 609-614. https://doi.org/10.1039/b208748k.
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