氟烷基磺酰氟和(2S,3R)-2,3-二羟基-3-苯基丙酸甲酯的脱水环氧化反应的研究

Study of Cyclodehydration of Methyl(2S,3R)-2,3-Dihydroxy-3-Phenylpropionate with Fluoroalkanesulfonyl Fluoride

考察了(2S,3R)-2,3-二羟基-3-苯基丙酸甲酯和几种常用的氟烷基磺酰氟试剂在有机碱存在下的脱水环氧化反应.实验结果表明,氟烷基磺酰氟能够诱导(2S,3R)-2,3-二羟基-3-苯基丙酸甲酯发生脱水环氧化反应而生成(2R,3R)-2,3-环氧-3-苯基丙酸甲酯,得率80%～92%,且产物的不对映过量(ee)值大于97%.该方法具有工业化应用前景.

The cyclodehydration of methyl（2S,3R）-2,3-dihydroxy-3-phenylpropionate with fluoroalkane-sulfonyl fluoride in the presence of an organic base was investigated in detail.The title cyclodehydration re-sulted in the smooth formation of methyl（2R,3R）-2,3-epoxy-3-phenylpropionate in one step in the yield of 80%～92%,and its enantiomeric excess value is higher than 97%.This new methodology is potentially applicable to industrial manufacturing of methyl（2R,3R）-2,3-epoxy-3-phenylpropionate,a key intermediate for the synthesis of Taxol side chain.