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Absolute Asymmetric Synthesis: Protected Substrate Oxidation

Journal article
Authors Susanne Olsson
Per Martin Björemark
Theonitsa Kokoli
J. Sundberg
Anders Lennartson
C. J. McKenzie
Mikael Håkansson
Published in Chemistry - A European Journal
Volume 21
Issue 13
Pages 5211-5219
ISSN 0947-6539
Publication year 2015
Published at Department of Chemistry and Molecular Biology
Pages 5211-5219
Language en
Links dx.doi.org/10.1002/chem.201406354
Keywords asymmetric synthesis, crystal growth, oxidation, ruthenium, sulfur ligands
Subject categories Inorganic Chemistry

Abstract

Three new conglomerates incorporating bidentate sulfide ligands coordinated by Ru-II centers have been prepared. Total spontaneous resolution by slow crystallization gives highly enantioenriched crystal batches, which are used in enantioselective oxidation of the sulfide ligands to give chiral sulfoxide complexes with >98% ee. All relevant stereoisomers have been characterized by single-crystal X-ray diffraction, CD spectroscopy, and chiral HPLC. If the ligand range can be extended to monodentate sulfides, a large-scale and recyclable process for enantioselective oxidation of sulfides can be designed.

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