lsoinversion Behavior in the Enantioselective Oxidations of Pyridylmethylthiobenzimidazoles to Chiral Proton Pump Inhibitors on Titanium Salalen Complexes Full article
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ACS Catalysis
ISSN: 2155-5435 |
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| Output data | Year: 2015, Volume: 5, Number: 8, Pages: 4673-4679 Pages count : DOI: 10.1021/acscatal.5b01212 | ||||||
| Tags | asymmetric oxidation; hydrogen peroxide; esomeprazole; isoinversion; mechanism; titanium | ||||||
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Abstract:
The oxidation of two pyridylmethylthiobenzimidazoles to proton pump inhibitors (S)-omeprazole and (R)lansoprazole, and to their enantiomers, with H2O2 is achieved by using chiral titanium salalen complexes as catalysts. The latter ensure high enantioselectivities (up to 96% ee) and efficiencies (TN 200-300), with high sulfoxide yields (up to >96%). The oxidation enantioselectivities vary with temperature in a nonmonotonic manner, demonstrating isoinversion behavior. Maximum enantioselectivity is attained at 273 ... 283 K, which temperature region may be recommended for preparative oxidations. Kinetic peculiarities and the oxidation mechanism are discussed.
Cite:
Talsi E.P.
, Rybalova T.V.
, Bryliakov K.P.
lsoinversion Behavior in the Enantioselective Oxidations of Pyridylmethylthiobenzimidazoles to Chiral Proton Pump Inhibitors on Titanium Salalen Complexes
ACS Catalysis. 2015. V.5. N8. P.4673-4679. DOI: 10.1021/acscatal.5b01212 WOS Scopus РИНЦ OpenAlex
lsoinversion Behavior in the Enantioselective Oxidations of Pyridylmethylthiobenzimidazoles to Chiral Proton Pump Inhibitors on Titanium Salalen Complexes
ACS Catalysis. 2015. V.5. N8. P.4673-4679. DOI: 10.1021/acscatal.5b01212 WOS Scopus РИНЦ OpenAlex
Dates:
| Published online: | Jul 10, 2015 |
| Published print: | Aug 7, 2015 |
Identifiers:
| Web of science: | WOS:000359395100021 |
| Scopus: | 2-s2.0-84938709566 |
| Elibrary: | 23996511 |
| OpenAlex: | W2511199642 |