PRACTICAL SYNTHESIS OF Z-UNSATURATED ESTERS BY USING A NEW HORNER-EMMONS REAGENT, ETHYL DIPHENYLPHOSPHONOACETATE
PRACTICAL SYNTHESIS OF Z-UNSATURATED ESTERS BY USING A NEW HORNER-EMMONS REAGENT, ETHYL DIPHENYLPHOSPHONOACETATE
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DOI：
10.1016/0040-4039(95)00726-s
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发表时间：
1995-06-05
影响因子：
1.8
通讯作者：
ANDO, K
中科院分区：
文献类型：
--
作者：
ANDO, K
以三乙基膦乙酸酯、PCl5和苯酚为原料，以60%的总收率制备了新的霍纳-埃蒙斯试剂二苯基膦乙酸乙酯1。在四氢呋喃中Tritons(R) B或NaH存在的情况下，1与醛的Horner-Emmons反应使z -不饱和酯具有89-93%的选择性，几乎定量产率。在Still条件下（KHMDS/18-crown-6）， 1具有99%的选择性。
A new Horner-Emmons reagent, ethyl diphenylphosphonoacetate 1 was prepared from triethyl phosphonoacetate, PCl5, and phenol in 60%, overall yield. Horner-Emmons reaction of 1 with aldehydes in the presence of Tritons(R) B or NaH in THF gave the Z-unsaturated esters in 89-93% selectivity in almost quantitative yields. Furthermore, 1 showed up to 99% Z-selectivity under Still's condition (KHMDS/18-crown-6).