Enantioselective Aromatic Sulfide Oxidation and Tandem Kinetic Resolution Using Aqueous H2O2 and Chiral Iron–Bis(oxazolinyl)bipyridine Catalysts. Issue 12 (29th March 2017)

• Record Type: Journal Article
• Authors: Jalba, Angela; Régnier, Noémie; Ollevier, Thierry
• Is Part Of: European journal of organic chemistry. Issue 12(2017)
• Page Start: 1628
• Page End: 1637
• Publication Date: 2017-03-29
• Subjects: Asymmetric catalysis -- Kinetic resolution -- Sulfoxides -- Iron -- Oxidation -- Enantioselectivity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601597
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An efficient method for the oxidation of aromatic sulfides has been developed by using aqueous H2 O2, catalyzed by the in situ generated chiral Fe/6, 6′‐bis(4‐isopropyloxazolin‐2‐yl)‐2, 2′‐bipyridine (bipybox‐ i Pr) complex. The corresponding sulfoxides were obtained with high enantioselectivities (up to 98.5:1.5 er ) and in good yields (up to 61 %) when the mono‐oxidation of the sulfides was performed in combination with the kinetic resolution of the sulfoxide into the sulfone. Abstract : An enantioselective oxidation of aromatic sulfides has been developed by using aqueous H2 O2, FeCl2, and the chiral 6, 6′‐bis(4‐isopropyloxazolin‐2‐yl)‐2, 2′‐bipyridine (bipybox‐ i Pr) ligand. The corresponding sulfoxides were obtained with high enantioselectivities and in good yields.