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Synlett 2001; 2001(4): 0501-0504
DOI: 10.1055/s-2001-12437
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Catalytic Asymmetric Dihydroxylation of C,C Double Bonds with Osmium Tetroxide Using Selenoxides as Co-oxidants

Alain Krief* , Catherine Castillo-Colaux
  • *Laboratoire de Chimie Organique de Synthèse, Département de Chimie, Facultés Universitaires Notre-Dame de la Paix, 61 rue de Bruxelles, B-5000 NAMUR, Belgium; Fax + 32(81)72 45 36; E-mail: alain.krief@fundp.ac.be
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Publication Date:
31 December 2001 (online)

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Asymmetric dihydroxylation of olefins has been achieved in good yields and ee's using potassium osmate dihydrate (K2OsO2(OH)4, the pre-oxidant), (DHQD)2PHAL (the chiral ligand), potassium carbonate (the base) and selenoxides (the co-oxidants). Both the yield and the ee proved to be pH dependent, the highest yield and ee being found at almost the same pH values. The rate of the reaction was found to be highly dependent upon the structure of the selenoxide used. Some representative examples involving aminoxides are presented for comparison.

alkenes - dihydroxylation - glycolysation - selenoxides - osmium tetroxide - oxidation