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Heterogeneous Bifunctional Catalysts for the Synthesis of Chiral Vicinal Diols

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Abstract

Heterogeneous bifunctional catalysts consisting of palladate–osmate and osmate–tungstate developed by the ion exchange on quaternary ammonium salts covalently bound to resin, and their homogeneous bimetallic analogs are evaluated for the synthesis of chiral vicinal diols. The heterogeneous bifunctional catalyst (resin-PdOs) and its homogeneous analog are used in the tandem Heck-asymmetric dihydroxylation (AD) to afford diols with excellent yields and enantiomeric excesses (ee's) in the presence of various co-oxidants. The other bifunctional catalyst (resin-OsW) and its homogeneous analog are used in a simultaneous asymmetric dihydroxylation-N-oxidation of a wide range of olefins to obtain chiral vicinal diols with higher yields and ee's using H2O2 as terminal oxidant. The bifunctional resin catalysts are recovered quantitatively by a simple filtration and reused for a number of cycles with consistent activity.

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Authors and Affiliations

  1. Inorganic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, 500 007, India

    Boyapati M. Choudary, Sateesh Madhi, Naidu S. Chowdari & Mannepalli L. Kantam

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  1. Boyapati M. Choudary
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  2. Sateesh Madhi
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  3. Naidu S. Chowdari
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  4. Mannepalli L. Kantam
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Choudary, B.M., Madhi, S., Chowdari, N.S. et al. Heterogeneous Bifunctional Catalysts for the Synthesis of Chiral Vicinal Diols. Topics in Catalysis 29, 183–187 (2004). https://doi.org/10.1023/B:TOCA.0000029801.51873.61

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