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lsoinversion Behavior in the Enantioselective Oxidations of Pyridylmethylthiobenzimidazoles to Chiral Proton Pump Inhibitors on Titanium Salalen Complexes Научная публикация

Журнал ACS Catalysis
ISSN: 2155-5435
Вых. Данные Год: 2015, Том: 5, Номер: 8, Страницы: 4673-4679 Страниц : DOI: 10.1021/acscatal.5b01212
Ключевые слова asymmetric oxidation; hydrogen peroxide; esomeprazole; isoinversion; mechanism; titanium
Авторы Talsi Evgenii P. 1,2 , Rybalova Tatyana V. 1,3 , Bryliakov Konstantin P. 1,2
Организации
1 (Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
2 (Данные Web of science) Boreskov Inst Catalysis, Novosibirsk 630090, Russia
3 (Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

Реферат: 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.
Библиографическая ссылка: 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
Даты:
Опубликована online: 10 июл. 2015 г.
Опубликована в печати: 7 авг. 2015 г.
Идентификаторы:
Web of science WOS:000359395100021
Scopus 2-s2.0-84938709566
РИНЦ 23996511
OpenAlex W2511199642
Альметрики: