1178871-13-0Relevant articles and documents
Sequential hiyaima coupling/narasaka acylation reaction of (e)-1,2-disilylethene: rapid assembly of α,β-unsaturated carbonyl motifs
Thiot, Carine,Mioskowski, Charles,Wagner, Alain
experimental part, p. 3219 - 3227 (2009/12/09)
The synthesis and application of (E)-1,2-disilylethene 5 as a central functional building block in a sequential Hiyama coupling/Narasaka acylation reaction are described, Its use in the rapid and versatile construction of α,β-unsaturated carbonyl motifs found in a number of polyunsaturated natural products has been demonstrated. It was observed that due to the differential intrinsic reactivity of the two carbon-silicon bonds, this bis-metallated lynchpin-type reagent is activated selectively and sequentially by Pd and Rh catalysis, negating the need for any protecting group, A number of (E)-α,β-unsaturated ketones were efficiently synthesized with complete chemoselectively in the presence of a variety of halides and anhydride acids. Conjugated polyunsaturated ketones and diversely α'-functionalized α,β-enones, such, as chalcones, a heterocyclic dienone and the highly conjugated ethyl (2Z,4E)-6-oxo-6-(2-thienyl)hexa-2,4-dienoate, were obtained in good overall yields. Thus, this coupling sequence provides a high degree of modularity, that is, a single template is likely to produce a large number of synthetic targets.
