- Iron-Catalyzed Reductive Ethylation of Imines with Ethanol
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The borrowing hydrogen strategy has been applied to the ethylation of imines with an air-stable iron complex as precatalyst. This approach opens new perspectives in this area as it enables the synthesis of unsymmetric tertiary amines from readily available substrates and ethanol as a C2 building block. A variety of imines bearing electron-rich aryl or alkyl groups at the nitrogen atom could be efficiently reductively alkylated without the need for molecular hydrogen. The mechanism of this reaction, which shows complete selectivity for ethanol over other alcohols, has been studied experimentally and by means of DFT computations.
- Vayer, Marie,Morcillo, Sara P.,Dupont, Jennifer,Gandon, Vincent,Bour, Christophe
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supporting information
p. 3228 - 3232
(2018/03/13)
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- An effective method to prepare imines from aldehyde, bromide/epoxide, and aqueous ammonia
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A three-component reaction of aldehydes, alkyl bromides, and ammonia to form imines was studied. Aqueous ammonia was applied as the nitrogen source and solvent in the reaction. For the aromatic aldehyde, the product yields are good to excellent and the reaction conditions are mild to be compatible with a range of functional groups. The reaction of aldehydes and aqueous ammonia with epoxides was also studied and imines bearing a vicinal hydroxyl group can be obtained efficiently and regioselectively. And studies showed that this method allows the synthesis of primary amines and especially 1,2-amino alcohol selectively in high yield. It is proposed that the reaction pathway might involve a key intermediate of hydrobenzamide.
- Huang, Jing-Mei,Zhang, Jue-Fei,Dong, Yi,Gong, Wen
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supporting information; experimental part
p. 3511 - 3514
(2011/06/22)
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- Syntheses of the opioid substructures 1,2,3,4,5,6-hexahydro-2,6-methano-3- benzazocine and 2,3,4,5-tetrahydro-1,5-methano-1H-2-benzazepine
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Concise syntheses of 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine (12) and 2,3,4,5-tetrahydro-1,5-methano-1H-2-benzazepine (18) are described and involve an intramolecular Friedel-Crafts alkylation and an intramolecular Heck cyclization as their respec
- Coe, Jotham W.,Brooks, Paige R.,Vetelino, Michael G.,Bashore, Crystal G.,Bianco, Krista,Flick, Andrew C.
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supporting information; experimental part
p. 953 - 954
(2011/03/18)
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- Enantioselective organocatalysis of Strecker and Mannich reactions based on carbohydrates
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Efficient organocatalysts for enantioselective Strecker and Mannich reactions were constructed from glucosamine as a readily accessible chiral scaffold. A variety of aromatic aldimines were subjected to hydrocyanation with good to excellent yield (72-98%)
- Becker, Christian,Hoben, Christine,Kunz, Horst
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p. 417 - 424
(2008/02/07)
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- A novel entry toward 2-imino-1,3-thiazolidines and 2-imino-1,3-thiazolines by ring transformation of 2-(thiocyanomethyl)aziridines
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(Chemical Equation Presented). A new, efficient, and straightforward synthesis of 3-arylmethyl-4-chloromethyl-2-imino-1,3-thiazolidines and 2-(N-acylimino)-3-arylmethyl-4-chloromethyl-1,3-thiazolidines has been developed by ring transformation of 1-arylme
- D'hooghe, Matthias,Waterinckx, Alex,De Kimpe, Norbert
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p. 227 - 232
(2007/10/03)
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- A straightforward and versatile synthetic approach to 1-azabicyclic alkaloids
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A very straightforward route to 1-azabicyclo alkaloid scaffolds with several ring sizes is reported. The final bicyclic structures were built through a synthetic scheme that involved (i) the construction of dienic 4-piperidone systems by an imino-Diels-Al
- Barluenga, Jose,Mateos, Carlos,Aznar, Fernando,Valdes, Carlos
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p. 7114 - 7122
(2007/10/03)
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