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Synlett 1991; 1991(11): 791-792
DOI: 10.1055/s-1991-20877
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Asymmetric Oxidation of Sulfides Catalyzed by a D4 -Symmetrical Manganese-Tetraphenylporphyrin

Ronald L. Halterman* , Shyi-Tai Jan, Heather L. Nimmons
  • *Department of Chemistry, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA
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Publication Date:
07 March 2002 (online)

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Aryl alkyl sulfides were oxidized enantioselectively to chiral sulfoxides in the presence of stoichiometric amounts of iodosylbenzene and catalytic amounts of a D4 -symmetrical manganese-tetraphenylporphyrin, 1 {chloro[5,10,15,20-tetrakis(1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracen-9-yl)-porphyrinato]manganese(III)}. The oxidations were complete within two hours at room temperature in methylene chloride using 0.5 mol% of the chiral catalyst and gave chemical yields above 82% and enantioselectivities ranging from 40 to 68% enantiomeric excess.