246509-58-0Relevant academic research and scientific papers
Preparation of homoallylic amines via a three-component coupling process
Battilocchio, Claudio,Labes, Ricardo,Ley, Steven V.,Ou, Xiaoxu
supporting information, p. 6652 - 6654 (2018/09/29)
A three-component synthesis of homoallylic amines is described. The allylboronic species were generated in situ by homologation of vinyl boroxines with trimethylsilyldiazomethane, then followed by trapping of the allylboron intermediate with imines. Twenty-seven compounds were successfully prepared in moderate to high yields. Imines bearing various functional groups were tolerated, including aliphatic, aromatic and heteroaromatic substituents. Further elaboration of some of the homoallylic amines to form azeditines is also reported.
Iron-Catalyzed Reductive Ethylation of Imines with Ethanol
Vayer, Marie,Morcillo, Sara P.,Dupont, Jennifer,Gandon, Vincent,Bour, Christophe
supporting information, p. 3228 - 3232 (2018/03/13)
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.
Palladium-catalyzed C-H activation of N-Allyl Imines: Regioselective allylic alkylations to deliver substituted aza-1,3-dienes
Trost, Barry M.,Mahapatra, Subham,Hansen, Martin
supporting information, p. 6032 - 6036 (2015/05/13)
A new mode of activation of an imine via a rare aza-substituted π-allyl complex is described. Palladium-catalyzed C(sp3)-H activation of the N-allyl imine and the subsequent nucleophilic attack by the α-alkyl cyanoester produced the 1-aza-1,3-d
Regio- and chemoselective intermolecular hydroamination of allyl imines for the synthesis of 1,2-diamines
Ickes, Andrew R.,Ensign, Seth C.,Gupta, Anil K.,Hull, Kami L.
supporting information, p. 11256 - 11259 (2014/09/29)
The synthesis of 1,2-diamines via a Rh-catalyzed intermolecular hydroamination of N-allyl imines with cyclic amines is presented. Coordinating groups proximal to the olefin bind to the catalyst and promote the transformation. The reaction affords 1,2-diam
Enantioselective organocatalysis of Strecker and Mannich reactions based on carbohydrates
Becker, Christian,Hoben, Christine,Kunz, Horst
, p. 417 - 424 (2008/02/07)
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%)
Electron transfer induced ring opening of 2-(bromomethyl)aziridines by magnesium in methanol
Tehrani, Kourosch Abbaspour,NguyenVan, Tuyen,Karikomi, Michinori,Rottiers, Mario,De Kimpe, Norbert
, p. 7145 - 7152 (2007/10/03)
Magnesium metal in methanol was used as a simple electron transfer induced ring-opening reagent of 2-(bromomethyl)aziridines to afford allylamines derivatives in 70-90% yield.
