Ti-Salan Catalyzed Asymmetric Sulfoxidation of Pyridylmethylthiobenzimidazoles to Optically Pure Proton Pump Inhibitors Научная публикация
| Конференция |
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 авг. - 4 сент. 2015 , Kazan |
||||
|---|---|---|---|---|---|
| Журнал |
Catalysis Today
ISSN: 0920-5861 , E-ISSN: 1873-4308 |
||||
| Вых. Данные | Год: 2017, Том: 279, Страницы: 84-89 Страниц : 6 DOI: 10.1016/j.cattod.2016.03.006 | ||||
| Ключевые слова | Asymmetric oxidation, Esomeprazole, Hydrogen peroxide, Isoinversion, Mechanism, Salan, Titanium | ||||
| Авторы |
|
||||
| Организации |
|
Информация о финансировании (1)
| 1 | Российский научный фонд | 14-13-00158 |
Реферат:
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.
Библиографическая ссылка:
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 CAPlusCA 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 CAPlusCA OpenAlex
Даты:
| Поступила в редакцию: | 15 окт. 2015 г. |
| Принята к публикации: | 14 мар. 2016 г. |
| Опубликована online: | 24 мар. 2016 г. |
| Опубликована в печати: | 1 янв. 2017 г. |
Идентификаторы БД:
| Web of science: | WOS:000388778100012 |
| Scopus: | 2-s2.0-85025669397 |
| РИНЦ: | 28256898 | 41783537 |
| Chemical Abstracts: | 2016:457025 |
| Chemical Abstracts (print): | 165:522547 |
| OpenAlex: | W2304497535 |