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Asymmetric synthesis of new chiral 1,2- and 1,3-diols

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Abstract

Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine–BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4 and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, 1H and 13C NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine–BH3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.

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Acknowledgments

This study was supported by the Istanbul University Department of Scientific Research Projects (İ.Ü. Bilimsel Araştırma Projeleri Birimi) with Project Number 3099.

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  1. Department of Chemistry, University of Istanbul, Istanbul, Turkey

    Tülay Yıldız & Ayşe Yusufoğlu

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  1. Tülay Yıldız
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  2. Ayşe Yusufoğlu
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Correspondence to Ayşe Yusufoğlu.

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Yıldız, T., Yusufoğlu, A. Asymmetric synthesis of new chiral 1,2- and 1,3-diols. Monatsh Chem 144, 183–190 (2013). https://doi.org/10.1007/s00706-012-0792-7

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  • DOI: https://doi.org/10.1007/s00706-012-0792-7

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