173416-02-9Relevant academic research and scientific papers
Homoallylic amines as efficient chiral inducing frameworks in the conjugate addition of amides to α,β-unsaturated esters. An entry to enantio-enriched diversely substituted amines
Anani, Lilia,Behr, Jean-Bernard,Coelho, Aurélien,Machado-Rodrigues, Carine,Massicot, Fabien,Rogier, Johann,Vasse, Jean-Luc
, p. 2632 - 2636 (2020/04/17)
The diastereoselective conjugate addition of secondary homoallylamines, obtained in the enantioenriched form via allylmetallation of imines, to α,β-unsaturated esters is reported. This method allows access to valuable building blocks as well as heterocyclic skeletons, providing tertiary amines bearing two chains integrating a stereogenic center adjacent to the nitrogen atom.
Chemoselective reductive nucleophilic addition to tertiary amides, secondary amides, and N-methoxyamides
Nakajima, Minami,Oda, Yukiko,Wada, Takamasa,Minamikawa, Ryo,Shirokane, Kenji,Sato, Takaaki,Chida, Noritaka
supporting information, p. 17565 - 17571 (2015/02/19)
As the complexity of targeted molecules increases in modern organic synthesis, chemoselectivity is recognized as an important factor in the development of new methodologies. Chemoselective nucleophilic addition to amide car-bonyl centers is a challenge because classical methods require harsh reaction conditions to overcome the poor elec-trophilicity of the amide carbonyl group. We have successfully developed a reductive nucleophilic addition of mild nu-cleophiles to tertiary amides, secondary amides, and N-methoxyamides that uses the Schwartz reagent [Cp2ZrHCl]. The reaction took place in a highly chemoselective fashion in the presence of a variety of sensitive functional groups, such as methyl esters, which conventionally require protection prior to nucleophilic addition. The reaction will be applicable to the concise synthesis of complex natural alkaloids from readily available amide groups.
The first example of asymmetric induction in an anionic amino-Cope rearrangement
Allin, Steven M.,Button, Martin A. C.
, p. 3345 - 3348 (2007/10/03)
The anionic amino-Cope rearrangement of suitably functionalized acyclic 3-amino-1,5-diene substrates has been achieved and we report the first example of an asymmetric anionic amino-Cope rearrangement to yield an enantiomerically enriched product (75% e.e.). The absolute stereochemistry of the products has been verified and transition state models are proposed to rationalize the stereochemical outcome.
Mg and Zn mediated allylation of imines with allyl bromide
Wang, De-Kun,Dai, Li-Xin,Hou, Xue-Long,Zhang, Yi
, p. 4187 - 4188 (2007/10/03)
Both aldimines and ketamines are allylated under simple Barbier-type conditions using allyl bromide and commercial magnesium foil or zinc dust in tetrahydrofuran at room temperature.
Allylstannane Allylation of Aldimines Activated by Chlorotrimethylsilane
Wang, De-Kun,Dai, Li-Xin,Hou, Xue-Long
, p. 8649 - 8652 (2007/10/02)
Aldimines activated by chlorotrimethylsilane reacted with allylstannane to give the corresponding homoallylic amines with excellent yields.
Metallic bismuth and tantalum mediated C-allylation of aldimines with allyl bromide
Bhuyan, Pulak J.,Prajapati, Dipak,Sandhu, Jagir S.
, p. 7975 - 7976 (2007/10/02)
A facile method for the synthesis of homoallyl amines using Bi/BU4NBr/MeCN and Ta/Bu4NBr/ THF system has been performed in a regiospecific manner.
