Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols |
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Authors: | Huang Kun Wang Haiyang Stepanenko Viatcheslav De Jesús Melvin Torruellas Carilyn Correa Wildeliz Ortiz-Marciales Margarita |
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Institution: | Department of Chemistry, University of Puerto Rico-H-umacao, CUH Station, Humacao, Puerto Rico 00791. |
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Abstract: | An enantioselective borane-mediated reduction of a variety of 2-haloketones with 10% spiroaminoborate ester 1 as catalyst is described. By a simple basic workup of 2-halohydrins, optically active epoxides are obtained in high yield and with excellent enantiopurity (up to 99% ee). Ring-opening of oxiranes with phenoxides or sodium azide is investigated under different reaction conditions affording nonracemic 1,2-hydroxy ethers and 1,2-azido alcohols with excellent enantioselectivity (99% ee) and in good to high chemical yield. |
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