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

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

Journal

ACS Catalysis
ISSN: 2155-5435

Output data

Year: 2015, Volume: 5, Number: 8, Pages: 4673-4679 Pages count : DOI: 10.1021/acscatal.5b01212

Tags

asymmetric oxidation; hydrogen peroxide; esomeprazole; isoinversion; mechanism; titanium

Authors

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

Affiliations

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

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.
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

Published online:	Jul 10, 2015
Published print:	Aug 7, 2015

Web of science	WOS:000359395100021
Scopus	2-s2.0-84938709566
Elibrary	23996511
OpenAlex	W2511199642