2012
DOI: 10.1021/ol300811e
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Abstract: A novel water-soluble Au(III)-NHC complex has been synthesized and successfully applied in the intramolecular cyclization of γ-alkynoic acids into enol-lactones under biphasic toluene/water conditions, thus representing a rare example of an active and selective catalyst for this transformation in aqueous media. Remarkably, competing alkyne hydration processes were not observed, even during the desymmetrization reaction of challenging 1,6-diyne substrates. In addition, after phase separation, the water-soluble … Show more

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Cited by 101 publications
(54 citation statements)
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“…the catalytic cycloisomerization of γ-alkynoic acids (Figure 2). 12 It is worth mentioning that this catalytic transformation provides an easy and atom-economical entry to enol-lactones, an important class of functionalized heterocycles useful as synthetic intermediates. Although a large number of catalysts able to convert γ-alkynoic acids into enol-lactones are already known, 13,14 most of the reported procedures require water-free reaction conditions.…”
mentioning
confidence: 99%
See 1 more Smart Citation
“…the catalytic cycloisomerization of γ-alkynoic acids (Figure 2). 12 It is worth mentioning that this catalytic transformation provides an easy and atom-economical entry to enol-lactones, an important class of functionalized heterocycles useful as synthetic intermediates. Although a large number of catalysts able to convert γ-alkynoic acids into enol-lactones are already known, 13,14 most of the reported procedures require water-free reaction conditions.…”
mentioning
confidence: 99%
“…Hydrogen atoms, except those on the N(3) atoms, have been omitted for clarity. (14) C(3)-N(1) 1.409(13) 1.367 (12) Angles 5b 5c…”
mentioning
confidence: 99%
“…Since then, a number of gold-based catalysts capable of operating in pure water or in aqueous biphasic mixtures have been described, most involving functionalized N-heterocyclic carbenes (NHC) as auxiliary ligands. In this regard, the groups of Michelet, Cadierno and Conejero developed the zwitterionic Au(III)-NHC complex 10b which proved to be active in the cycloisomerization of a broad range of γ-alkynoic acids under biphasic toluene/water conditions (Scheme 6) [44]. Remarkably, the participation of a silver(I) co-catalyst, usually employed in catalytic gold chemistry to generate vacant coordination sites on the metal through chloride ligands abstraction, was not required.…”
Section: Cycloisomerization Of Preformed or In Situ Generated Alkynoimentioning
confidence: 99%
“…the cycloisomerization of alkynoic acids. [58][59][60][61][62][63] However, we would like to stress that these intramolecular reactions are favoured from a thermodynamic point of view and do not represent a notable synthetic problem. 52,64 Another challenging aspect related with the use of internal alkynes concerns the control of the regio-and stereoselectivity of the addition process since, starting from non-symmetrically substituted substrates R ), up to four isomeric enol esters can be formed (obviously difficult to separate).…”
Section: Introductionmentioning
confidence: 99%