Use of lithium hexafluoroisopropoxide as a mild base for Horner-Wadsworth-Emmons olefination of epimerizable aldehydes.
[reaction: see text] The weak base lithium 1,1,1,3,3,3-hexafluoroisopropoxide (LiHFI) is shown to be highly effective as a reagent for intermolecular Horner-Wadsworth-Emmons (HWE) olefination of epimerizable aldehydes with trimethyl phosphonoacetate, affording products with little or no epimerization and notably high E-selectivity.
Blasdel
Landy K
LK
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Myers
Andrew G
AG