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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
Authors:Huang Kun  Wang Haiyang  Stepanenko Viatcheslav  De Jesús Melvin  Torruellas Carilyn  Correa Wildeliz  Ortiz-Marciales Margarita
Institution:Department of Chemistry, University of Puerto Rico-H-umacao, CUH Station, Humacao, Puerto Rico 00791.
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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