Investigation of the titanium-mediated catalytic enantioselective oxidation of aryl benzyl sulfides containing heterocyclic groups
Capozzi, Maria Annunziata M. (Università di Bari. Dipartimento di Chimica)
Alvarez-Larena, Angel (Universitat Autònoma de Barcelona. Servei de Difracció de Raigs X)
Piniella Febrer, Joan F. (Universitat Autònoma de Barcelona. Departament de Geologia)
Cardellicchio, Cosimo (Università di Bari. Dipartimento di Chimica)

Date:	2024
Abstract:	Our enantioselective oxidation protocol, based upon hydroperoxides in the presence of a titanium/(S,S)-hydrobenzoin catalyst, was tested for the first time with aryl benzyl sulfides containing heterocyclic moieties (2-thienyl, 2-pyridyl and benzimidazolyl), two of them being connected with the blockbuster omeprazole drug. Good yields of enantiopure sulfoxides were obtained in most cases. Two exceptions of unsatisfactory enantioselectivity in the oxidation of benzimidazolyl sulfides are reported. However, one of them was solved by crystallization of an enantio-enriched mixture. The present work was supported also by X-ray diffraction analysis of some synthesized sulfoxides and by energetic calculation of the crystal structures. The unexpected result is that the crystal structures of the racemic mixture of the two problematic benzimidazolyl sulfoxides are composed of separate enantiomers (a conglomerate), an interesting result that could be exploited in the future for the separation of the enantiomers of these sulfoxides.
Rights:	Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, la comunicació pública de l'obra i la creació d'obres derivades, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original.
Language:	Anglès
Document:	Article ; recerca ; Versió publicada
Published in:	RSC advances, Vol. 14, Issue 47 (November 2024) , p. 35105-35113, ISSN 2046-2069

DOI: 10.1039/d4ra07088g
PMID: 39497765

9 p, 683.6 KB

The record appears in these collections:
Articles > Research articles
Articles > Published articles