Ti-Salan Catalyzed Asymmetric Sulfoxidation of Pyridylmethylthiobenzimidazoles to Optically Pure Proton Pump Inhibitors Full article
| Conference |
11th European Workshop on Selective Oxidation - Selectivity in Oxidation - Key to New Resources Valorization (ISO) during the 12th European Congress on Catalysis - Balancing the Use of Fossil and Renewable Resources (Europacat) 30 Aug - 4 Sep 2015 , Kazan |
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| Journal |
Catalysis Today
ISSN: 0920-5861 , E-ISSN: 1873-4308 |
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| Output data | Year: 2017, Volume: 279, Pages: 84-89 Pages count : 6 DOI: 10.1016/j.cattod.2016.03.006 | ||||
| Tags | Asymmetric oxidation, Esomeprazole, Hydrogen peroxide, Isoinversion, Mechanism, Salan, Titanium | ||||
| Authors |
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| Affiliations |
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Funding (1)
| 1 | Russian Science Foundation | 14-13-00158 |
Abstract:
The asymmetric sulfoxidation of two pyridylmethylthiobenzimidazoles to anti-ulcer drugs of the PPI family (S)-omeprazole and (R)-lansoprazole with hydrogen peroxide, mediated by a series of chiral titanium(IV) salan complexes is reported. High sulfoxide yields (up to >95%) and enantioselectivities (up to 94% ee) have been achieved. The introduction of electron-withdrawing substituents leads to less active and less enantioselective catalysts. Like for the previously reported Ti-salalen catalyzed sulfoxidations, the temperature dependence of the sulfoxidation enantioselectivity in the presence of Ti-salan complexes is nonmonotonic, demonstrating isoinversion behavior with decreasing temperature. The oxidation is likely rate-limited by the formation of the active (presumably peroxotitanium(IV)) species, followed by a faster oxygen transfer to the substrate.
Cite:
Talsi E.P.
, Bryliakov K.P.
Ti-Salan Catalyzed Asymmetric Sulfoxidation of Pyridylmethylthiobenzimidazoles to Optically Pure Proton Pump Inhibitors
Catalysis Today. 2017. V.279. P.84-89. DOI: 10.1016/j.cattod.2016.03.006 WOS Scopus РИНЦ РИНЦ ANCAN OpenAlex
Ti-Salan Catalyzed Asymmetric Sulfoxidation of Pyridylmethylthiobenzimidazoles to Optically Pure Proton Pump Inhibitors
Catalysis Today. 2017. V.279. P.84-89. DOI: 10.1016/j.cattod.2016.03.006 WOS Scopus РИНЦ РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | Oct 15, 2015 |
| Accepted: | Mar 14, 2016 |
| Published online: | Mar 24, 2016 |
| Published print: | Jan 1, 2017 |
Identifiers:
| Web of science: | WOS:000388778100012 |
| Scopus: | 2-s2.0-85025669397 |
| Elibrary: | 28256898 | 41783537 |
| Chemical Abstracts: | 2016:457025 |
| Chemical Abstracts (print): | 165:522547 |
| OpenAlex: | W2304497535 |