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For similar three-component syntheses of homoallylic amines based on the in situ generation of acylimines, see
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For an excellent overview of the nucleophilicity of arenes as well as the reactivity of various other molecules, we recommend the database of Prof. H. Mayr (LMU Munich): http://www.cup.lmu.de/oc/mayr/reaktionsdatenbank/.
-
For an excellent overview of the nucleophilicity of arenes as well as the reactivity of various other molecules, we recommend the database of Prof. H. Mayr (LMU Munich): http://www.cup.lmu.de/oc/mayr/reaktionsdatenbank/.
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3, see the Supporting Information.
-
3, see the Supporting Information.
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61
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84887618867
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3+ species under our reaction conditions.
-
3+ species under our reaction conditions.
-
-
-
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62
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84887619660
-
-
3: 38 €/g]. Prices obtained from Alfa Aesar on 08/02/2013.
-
3: 38 €/g]. Prices obtained from Alfa Aesar on 08/02/2013.
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84887626267
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-
The reaction with phenol gives the glycine derivative in <10 % yield as a result of competitive oxidative coupling reactions.
-
The reaction with phenol gives the glycine derivative in <10 % yield as a result of competitive oxidative coupling reactions.
-
-
-
-
66
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84887625568
-
-
All the reactions shown were performed with the technical, unpurified polymer form of ethyl glyoxylate.
-
All the reactions shown were performed with the technical, unpurified polymer form of ethyl glyoxylate.
-
-
-
-
67
-
-
77954117971
-
-
Monomeric ethyl glyoxalate can be obtained by pyrolysis and purification by vacuum distillation. The monomeric form is very reactive and either polymerizes rapidly or reacts with water to form the hydrate. Therefore, monomeric ethyl glyoxalate has to be prepared just prior to use and handled under anhydrous conditions, see:, and references cited therein.
-
Monomeric ethyl glyoxalate can be obtained by pyrolysis and purification by vacuum distillation. The monomeric form is very reactive and either polymerizes rapidly or reacts with water to form the hydrate. Therefore, monomeric ethyl glyoxalate has to be prepared just prior to use and handled under anhydrous conditions, see:, T. Urushima, Y. Yasui, H. Ishikawa, Y. Hayashi, Org. Lett. 2010, 12, 2966-2969, and references cited therein.
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69
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84887623860
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Secondary amides or sulfonamides did not react under our reaction conditions.
-
Secondary amides or sulfonamides did not react under our reaction conditions.
-
-
-
-
70
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33750188274
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Angew. Chem. Int. Ed. 2006, 45, 4900 - 4921.
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84887619634
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See the Supporting Information for experimental details.
-
See the Supporting Information for experimental details.
-
-
-
-
72
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84887624027
-
-
Reactions with indoles not bearing electron-withdrawing N-protecting groups or other very reactive heteroarenes led to the exclusive formation of bis(heteroaryl)methanes.
-
Reactions with indoles not bearing electron-withdrawing N-protecting groups or other very reactive heteroarenes led to the exclusive formation of bis(heteroaryl)methanes.
-
-
-
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