Asymmetric Sulfoxidation of Thioanisole by Helical Ti(IV) Salan Catalysts

A new helix-directing salan ligand (R,R)-2 with the (1R,2R)-diaminocyclohexyl backbone and benz[a]anthryl sidearms was synthesized by borohydride reduction of the corresponding salen ligand. Formylation and reduction of (R,R)-2 yielded the N-Me counterpart, (R,R)-3. Complexation of these flexible li...

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Veröffentlicht in:	Chemistry letters 2012, Vol.41 (9), p.974-975
Hauptverfasser:	Barman, Sanmitra, Patil, Smita, Levy, Christopher J
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Sprache:	eng
Schlagworte:	Asymmetry Borohydrides Catalysis Catalysts Complexation Hydrogen peroxide Ligands Reduction
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description	A new helix-directing salan ligand (R,R)-2 with the (1R,2R)-diaminocyclohexyl backbone and benz[a]anthryl sidearms was synthesized by borohydride reduction of the corresponding salen ligand. Formylation and reduction of (R,R)-2 yielded the N-Me counterpart, (R,R)-3. Complexation of these flexible ligands to TiCl4 produced the [TiCl2(salan)] complexes (R,R)-4 and (R,R)-5, which were characterized by NMR, IR, and HRMS techniques. The complexes were tested as catalysts for the asymmetric sulfoxidation of thioanisole with cumene hydroperoxide and hydrogen peroxide as the oxidants. Modest selectivity was observed, with the N-H salan complex showing somewhat better chiral induction.
doi_str_mv	10.1246/cl.2012.974
format	Article
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source	Oxford University Press Journals All Titles (1996-Current)
subjects	Asymmetry Borohydrides Catalysis Catalysts Complexation Hydrogen peroxide Ligands Reduction
title	Asymmetric Sulfoxidation of Thioanisole by Helical Ti(IV) Salan Catalysts
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