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N-Heterocyclic Carbene (NHC) Catalyzed Cycloaddition of CO2 to N-Tosyl Aziridines: Regio and Stereoselective Synthesis of Oxazolidin-2-ones

Authors

  • Dr. Jayasree Seayad,

    Corresponding author
    1. Organic Chemistry, Institute of Chemical and Engineering Sciences, 8 Biomedical grove, Neuros, #07-01, Singapore 138665 (Singapore), Fax: (+65) 6464-2102
    • Organic Chemistry, Institute of Chemical and Engineering Sciences, 8 Biomedical grove, Neuros, #07-01, Singapore 138665 (Singapore), Fax: (+65) 6464-2102
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  • Dr. Abdul Majeed Seayad,

    1. Organic Chemistry, Institute of Chemical and Engineering Sciences, 8 Biomedical grove, Neuros, #07-01, Singapore 138665 (Singapore), Fax: (+65) 6464-2102
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  • Dr. Joseph Kok Peng Ng,

    1. Organic Chemistry, Institute of Chemical and Engineering Sciences, 8 Biomedical grove, Neuros, #07-01, Singapore 138665 (Singapore), Fax: (+65) 6464-2102
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  • Dr. Christina Li Lin Chai

    Corresponding author
    1. Organic Chemistry, Institute of Chemical and Engineering Sciences, 8 Biomedical grove, Neuros, #07-01, Singapore 138665 (Singapore), Fax: (+65) 6464-2102
    2. Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543 (Singapore)
    • Organic Chemistry, Institute of Chemical and Engineering Sciences, 8 Biomedical grove, Neuros, #07-01, Singapore 138665 (Singapore), Fax: (+65) 6464-2102
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Abstract

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NHC pumping on your stereo: A general N-heterocyclic carbene (NHC) catalyzed methodology for insertion of CO2 into N-tosyl aziridines giving 3,5-disubstituted and 3,4,5-trisubstituted oxazolidin-2-ones is developed. This method is also applied for the stereoselective synthesis of (4R,5R)-4-methyl-5-phenyloxazolidin-2-one.

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