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

Isoinversion 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 : 7 DOI: 10.1021/acscatal.5b01212

Авторы

Talsi Evgenii P. ^1,2 , Rybalova Tatyana V. ^1,3 , Bryliakov Konstantin P. ^1,2

Организации

1	Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russian Federation
2	Boreskov Institute of Catalysis, Pr. Lavrentieva 5, Novosibirsk 630090, Russian Federation
3	Vorozhtsov Novosibirsk Institute of Organic Chemistry, Pr. Lavrentieva 9, Novosibirsk 630090, Russian Federation

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.

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 CAPlusCA OpenAlex Sciact

Поступила в редакцию:	10 июн. 2015 г.
Опубликована online:	10 июл. 2015 г.
Опубликована в печати:	7 авг. 2015 г.

Web of science:	WOS:000359395100021
Scopus:	2-s2.0-84938709566
РИНЦ:	23996511
Chemical Abstracts:	2015:1148771
Chemical Abstracts (print):	163:217882
OpenAlex:	W2511199642
Sciact:	7615

БД	Цитирований
Scopus	36
OpenAlex	39