Copper-Catalyzed Asymmetric Oxidation of Sulfides.

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TY  - JOUR
  - O'Mahony GE, Ford A, Maguire AR
  - 2012
  - March
  - The Journal of Organic Chemistry
  - Copper-Catalyzed Asymmetric Oxidation of Sulfides.
  - Published
  - Altmetric: 1 ()
  - Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of the oxidation has been observed, with up to 93% ee for 2-naphthylmethyl phenyl sulfoxide, in modest yield in this instance (up to 30%). The influence of variation of solvent and ligand structure was examined, and the optimized conditions were then used to oxidize a number of aryl alkyl and aryl benzyl sulfides, producing sulfoxides in excellent yields in most cases (up to 92%), and good enantiopurities in certain cases (up to 84% ee).
  - 10.1021/jo2026178
DA  - 2012/03
ER  - 
@article{V132615233,
   = {O'Mahony GE,  Ford A and  Maguire AR },
   = {2012},
   = {March},
   = {The Journal of Organic Chemistry},
   = {Copper-Catalyzed Asymmetric Oxidation of Sulfides.},
   = {Published},
   = {Altmetric: 1 ()},
   = {{Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of the oxidation has been observed, with up to 93% ee for 2-naphthylmethyl phenyl sulfoxide, in modest yield in this instance (up to 30%). The influence of variation of solvent and ligand structure was examined, and the optimized conditions were then used to oxidize a number of aryl alkyl and aryl benzyl sulfides, producing sulfoxides in excellent yields in most cases (up to 92%), and good enantiopurities in certain cases (up to 84% ee).}},
   = {10.1021/jo2026178},
  source = {IRIS}
}
AUTHORSO'Mahony GE, Ford A, Maguire AR
YEAR2012
MONTHMarch
JOURNAL_CODEThe Journal of Organic Chemistry
TITLECopper-Catalyzed Asymmetric Oxidation of Sulfides.
STATUSPublished
TIMES_CITEDAltmetric: 1 ()
SEARCH_KEYWORD
VOLUME
ISSUE
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END_PAGE
ABSTRACTCopper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of the oxidation has been observed, with up to 93% ee for 2-naphthylmethyl phenyl sulfoxide, in modest yield in this instance (up to 30%). The influence of variation of solvent and ligand structure was examined, and the optimized conditions were then used to oxidize a number of aryl alkyl and aryl benzyl sulfides, producing sulfoxides in excellent yields in most cases (up to 92%), and good enantiopurities in certain cases (up to 84% ee).
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DOI_LINK10.1021/jo2026178
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