Literature DB >> 25677197

Absolute asymmetric synthesis: protected substrate oxidation.

Susanne Olsson1, Per Martin Björemark, Theonitsa Kokoli, Jonas Sundberg, Anders Lennartson, Christine J McKenzie, Mikael Håkansson.   

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.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric synthesis; crystal growth; oxidation; ruthenium; sulfur ligands

Year:  2015        PMID: 25677197     DOI: 10.1002/chem.201406354

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  3 in total

1.  Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening.

Authors:  Anthonius H J Engwerda; Niels Koning; Paul Tinnemans; Hugo Meekes; F Matthias Bickelhaupt; Floris P J T Rutjes; Elias Vlieg
Journal:  Cryst Growth Des       Date:  2017-07-03       Impact factor: 4.076

2.  Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess.

Authors:  Arimasa Matsumoto; Takaaki Abe; Atsushi Hara; Takayuki Tobita; Taisuke Sasagawa; Tsuneomi Kawasaki; Kenso Soai
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-23       Impact factor: 15.336

3.  Asymmetric Induction by a Nitrogen 14 N/15 N Isotopomer in Conjunction with Asymmetric Autocatalysis.

Authors:  Arimasa Matsumoto; Hanae Ozaki; Shunya Harada; Kyohei Tada; Tomohiro Ayugase; Hitomi Ozawa; Tsuneomi Kawasaki; Kenso Soai
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-18       Impact factor: 15.336

  3 in total

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