Isoinversion Behavior in the Enantioselective Oxidations of Pyridylmethylthiobenzimidazoles to Chiral Proton Pump Inhibitors on Titanium Salalen Complexes Full article
| Journal |
ACS Catalysis
ISSN: 2155-5435 |
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| Output data | Year: 2015, Volume: 5, Number: 8, Pages: 4673-4679 Pages count : 7 DOI: 10.1021/acscatal.5b01212 | ||||||
| Tags | asymmetric oxidation, esomeprazole, hydrogen peroxide, isoinversion, mechanism, titanium | ||||||
| Authors |
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| Affiliations |
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Funding (2)
| 1 | Federal Agency for Scientific Organizations | V.44.2.4. |
| 2 | Russian Foundation for Basic Research | 14-03-00102 |
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.
Isoinversion 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 ANCAN OpenAlex
Isoinversion 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 ANCAN OpenAlex
Dates:
| Submitted: | Jun 10, 2015 |
| Published online: | Jul 10, 2015 |
| Published print: | Aug 7, 2015 |
Identifiers:
| Web of science: | WOS:000359395100021 |
| Scopus: | 2-s2.0-84938709566 |
| Elibrary: | 23996511 |
| Chemical Abstracts: | 2015:1148771 |
| Chemical Abstracts (print): | 163:217882 |
| OpenAlex: | W2511199642 |