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Synthesis of Chiral Ligands with Multiple Stereogenic Centers and Their Application in Titanium(IV)-Catalyzed Enantioselective Desymmetrization of meso-Epoxides

Authors

  • Manish Kumar,

    1. Discipline of Inorganic Materials and Catalysis
    2. Academy of Scientific and Innovative Research, Central Salt and Marine Chemicals Research Institute (CSMCRI), Council of Scientific & Industrial Research (CSIR), G. B. Marg, Bhavnagar - 364 021, Gujarat (India), Fax: (+91) 0278-2566970
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  • Dr. Rukhsana I. Kureshy,

    Corresponding author
    1. Discipline of Inorganic Materials and Catalysis
    2. Academy of Scientific and Innovative Research, Central Salt and Marine Chemicals Research Institute (CSMCRI), Council of Scientific & Industrial Research (CSIR), G. B. Marg, Bhavnagar - 364 021, Gujarat (India), Fax: (+91) 0278-2566970
    • Discipline of Inorganic Materials and Catalysis
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  • Debashis Ghosh,

    1. Discipline of Inorganic Materials and Catalysis
    2. Academy of Scientific and Innovative Research, Central Salt and Marine Chemicals Research Institute (CSMCRI), Council of Scientific & Industrial Research (CSIR), G. B. Marg, Bhavnagar - 364 021, Gujarat (India), Fax: (+91) 0278-2566970
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  • Dr. Noor-ul H. Khan,

    1. Discipline of Inorganic Materials and Catalysis
    2. Academy of Scientific and Innovative Research, Central Salt and Marine Chemicals Research Institute (CSMCRI), Council of Scientific & Industrial Research (CSIR), G. B. Marg, Bhavnagar - 364 021, Gujarat (India), Fax: (+91) 0278-2566970
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  • Dr. Sayed H. R. Abdi,

    1. Discipline of Inorganic Materials and Catalysis
    2. Academy of Scientific and Innovative Research, Central Salt and Marine Chemicals Research Institute (CSMCRI), Council of Scientific & Industrial Research (CSIR), G. B. Marg, Bhavnagar - 364 021, Gujarat (India), Fax: (+91) 0278-2566970
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  • Dr. Hari C. Bajaj

    1. Discipline of Inorganic Materials and Catalysis
    2. Academy of Scientific and Innovative Research, Central Salt and Marine Chemicals Research Institute (CSMCRI), Council of Scientific & Industrial Research (CSIR), G. B. Marg, Bhavnagar - 364 021, Gujarat (India), Fax: (+91) 0278-2566970
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Abstract

New chiral ligands, (S,R,S)-1, (S,S,S)-1, (S,S,R)-1, (S,R,R)-1, (R,R,R)-1, (R,R,S)-1, (R,S,S)-1, (R,S,R)-1, (S,R,S)-2, (S,S)-3 and (R,S)-4 with diverse stereogenic centers arising from various diastereomeric combinations of aminoalcohol functionality with (R)- and (S)-1,1-binaphthol, were prepared and characterized. Catalytically active Ti complexes were generated in situ in the presence of water for the enantioselective ring-opening reaction of meso-stilbene oxide, cyclohexene oxide, cyclopentene oxide, and cis-butene oxide with different anilines as nucleophile. Significantly, catalysts Ti-(S,R,S)-1 and Ti-(R,S,S)-1 (15 mol %) produced syn-beta-amino alcohols of meso-stilbene oxide with (1S,2S) and (1R,2R) configuration respectively in excellent yields (>98 %) and enantioselectivities (ee value >99 %) in 10 h at room temperature. However, aliphatic/cyclic epoxides with aniline gave better performance with the catalyst Ti-(S,R,R)-1. The complex Ti-(S,R,S)-1 was successfully subjected to catalyst recovery and recyclability experiments over 6 cycles in the asymmetric ring-opening of meso-stilbene oxide with aniline with retention of performance.

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