Synlett · 1998 · 32 citations · 0 references
Natural SciencesChemistryOrganic ChemistryCross-coupling ReactionsOrganic SynthesisRetrosynthetic AnalysisAllylic FunctionalizationConjugated DienesHeterocycle FunctionalizationStereoselective Cross-couplingStille Coupling
(opens in new window) Buy Article (opens in new window) Permissions and Reprints (opens in new window) All articles of this category (opens in new window) Stereoselective construction of 3-trifluoromethyl conjugated dienoates or enynoates was achieved from ethyl ( Z )-4,4,4-trifluoro-3-iodobutenoate and alkenyltin or alkynyltin reagents through the Stille reaction. Reduction of ethyl 3-trifluoromethyldienoates using DIBAL-H selectively afforded allylic alcohols. conjugated 3-trifluoromethyl dienoates or dienols - Stille cross-coupling reaction - vinyltin reagents - vinylic iodide - substitution - reduction