期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 6, 页码 1883-1886出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo102294j
关键词
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资金
- National Institute of Health through their MBRS [GM 08216]
- NIH-INBRE [NC P20 RR-016470]
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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