Prop-2-yn-1-als and 1-phenylprop-2-yn-1-one in the chalcogen Baylis–Hillman reaction

Медведева, А. С.; Демина, М. М.; Novopashin, P. S.; Sarapulova, G. I.; Afonin, A. V.

doi:10.1070/mc2002v012n03abeh001553

Cited by 6 publications

(3 citation statements)

References 11 publications

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“…The chalcogen version133 of this reaction also gave “aldol adducts” 98 with excellent E stereoselectivity when the ketone was used, but moderate to good Z selectivity with esters (Scheme ) 134…”

Section: Titanium(iv) Enolates In Morita–baylis–hillman Reactionsmentioning

confidence: 98%

Titanium Enolate Chemistry at the Beginning of the 21st Century

2016

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Section: Titanium(iv) Enolates In Morita–baylis–hillman Reactionsmentioning

confidence: 98%

Titanium Enolate Chemistry at the Beginning of the 21st Century

2016

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“…68 The structure of propynal considerably affects the yield of the adduct: in case of trimethylsilyl and phenylpropynals, it is 70 and 52%, respectively, while for triethylgermylpropynal does not exceed 27%. Unsatis factory yield of compound 11b can be apparently explained by the heterolysis of the Ge-C sp bond in molecule 2b and formation of unstable products.…”

Section: The Baylis-hillman Reactionmentioning

confidence: 98%

Silicon- and germanium-substituted propynals as ambident electrophiles for the design of new heterocycles and polyfunctional acetylenes

2008

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Research results on the reactivity of silicon and germanium substituted propynals as ambident electrophiles in the reactions with mono and binucleophiles were summarized. Chemo and regioselectivity of the nucleophilic addition and cycloaddition depending on the structure of propynals, the nature of a reagent, catalyst, and the reaction conditions was studied. Wide synthetic potentialities of substituted propynals in the synthesis of new heterocyclic systems and polyfunctional acetylenes were demonstrated.

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“…Element-substituted propynals are used in the total synthesis of natural cytostatics, phorboxazoles 8 (inhibitors of thrombocytes aggregation), xemilofiban, 9 as well as for the preparation of 1H-1,2,3-triazolecarbaldehydes, 10 3,4-dihydropyrimidin-2-ones, 11 [(trimethylsilyl)ethynyl]-4H-pyran-3,5-dicarbaldehyde, 12 imidazo[1,2-a]pyridine-3-carbaldehydes, 13 silicon(germanium)-containing ynimines and enynes, 14 substituted porphyrins, 15 and polyfunctional Baylis-Hillman adducts. 16 One of the most widespread methods for the synthesis of propynals is by the oxidation of the corresponding acetylenic alcohols using different oxidants such as activated manganese dioxide, 17 chromium(VI) compounds, 18 dimethyl sulfoxide (Swern oxidation), 19 titanium(IV) chloride-triethylamine complex, 20 and molecular oxygen in the presence of an oxovanadium complex. 21 Activated manganese dioxide and pyridinium chlorochromate are the most commonly used reagents for this purpose.…”

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confidence: 99%