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Absolute Asymmetric Synthesis: Protected Substrate Oxidation
Author(s) -
Olsson Susanne,
Björemark Per Martin,
Kokoli Theonitsa,
Sundberg Jonas,
Lennartson Anders,
McKenzie Christine J.,
Håkansson Mikael
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406354
Subject(s) - enantioselective synthesis , denticity , sulfoxide , chemistry , sulfide , crystallization , substrate (aquarium) , single crystal , kinetic resolution , ligand (biochemistry) , stereochemistry , combinatorial chemistry , crystal structure , organic chemistry , crystallography , catalysis , biochemistry , geology , oceanography , receptor
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.