Tetrahedron Letters p. 4105 - 4108 (1995)
Update date:2022-08-11
Topics:
Ando, Kaori
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 Triton 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).
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