2017
DOI: 10.1002/adsc.201601092
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Gold‐Catalyzed 1,4‐Carbooxygenation of 3‐En‐1‐ynamides with Allylic and Propargylic Alcohols via Non‐Claisen Pathways

Abstract: Gold-catalyzed 1,4-carbooxygenations of 3-en-1-ynamides with allylic alcohols andpropargylic alcohols yield a,b-unsaturated amidest hrough non-Claisenp athways;t he mechanisms involve ionization of the initial gold enol ethers to form Cbound gold dienolates that capture allylicorpropargylic cations to yield the observedp roducts. Our 18 O-labeling experiments exclude ad irect gold-catalyzed allylation or propargylation on these 3-en-1ynamides.

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Cited by 20 publications
(13 citation statements)
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“…[17] To a solution of E-3a (70.45 mg, 0.20 mmol) in anhydrous toluene (1.0 mL) was added trimethylsilylacetylene (29.47 mg, 0.30 mmol), Et 3 N (30.36 mg, 0.30 mmol), CuI (3.80 mg, 0.02 mmol) and PdCl 2 (PPh 3 ) 2 (7.02 mg, 0.01 mmol). [17] To a solution of E-3a (70.45 mg, 0.20 mmol) in anhydrous toluene (1.0 mL) was added trimethylsilylacetylene (29.47 mg, 0.30 mmol), Et 3 N (30.36 mg, 0.30 mmol), CuI (3.80 mg, 0.02 mmol) and PdCl 2 (PPh 3 ) 2 (7.02 mg, 0.01 mmol).…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…[17] To a solution of E-3a (70.45 mg, 0.20 mmol) in anhydrous toluene (1.0 mL) was added trimethylsilylacetylene (29.47 mg, 0.30 mmol), Et 3 N (30.36 mg, 0.30 mmol), CuI (3.80 mg, 0.02 mmol) and PdCl 2 (PPh 3 ) 2 (7.02 mg, 0.01 mmol). [17] To a solution of E-3a (70.45 mg, 0.20 mmol) in anhydrous toluene (1.0 mL) was added trimethylsilylacetylene (29.47 mg, 0.30 mmol), Et 3 N (30.36 mg, 0.30 mmol), CuI (3.80 mg, 0.02 mmol) and PdCl 2 (PPh 3 ) 2 (7.02 mg, 0.01 mmol).…”
Section: Methodsmentioning
confidence: 99%
“…[14] The presence of carbon-bromine bond can be subsequently used in a series of coupling reaction. [17] [16] Furthermore, introducing trimethylsilylacetylene to E-3a could also take place catalyzed by palladium, providing conjugated enyne E-13d in 80% yield.…”
Section: Scheme 3 Plausible Reaction Mechanismmentioning
confidence: 99%
“…90 Finally, it should be mentioned that non-Claisen pathways have been reported in the gold-catalyzed reaction between enynamides and highly activated allylic and propargylic alcohols. 91…”
Section: Trapping Activated Keteniminium Ions With Nucleophiles and Smentioning
confidence: 99%
“…[76b] Liu and co-workers discovered that 1,4-carbooxygenation of 3-en-1-ynamides with the propargylic alcohols took place in the presence of a cationic gold(I) catalyst (Scheme 60). [77] A series of propargylic alcohols participated in the reaction to furnish the 1,4-carbooxygenation products bearing an internal alkyne group in up to 78% yield. The authors suggest that the transformation would proceed through the oxyauration of the activated 3-ene-1-ynamides with the propargylic alcohol followed by the intramolecular addition of a gold dienolate to a propargylic cation species.…”
Section: Gold Catalysismentioning
confidence: 99%