4383-23-7Relevant articles and documents
Synthesis of homoallylic amines via N-acyliminium ion reactions on solid support
Meester, Wim J. N.,Rutjes, Floris P. J. T.,Hermkens, Pedro H. H.,Hiemstra, Henk
, p. 1601 - 1604 (1999)
The synthesis of a library of homoallylic amines is reported. The key step in the synthesis is a one-pot N-acyliminium ion coupling involving a solid phase-bound carbamate, an aldehyde and an allylsilane under Lewis acid conditions.
Directed Nickel-Catalyzed Diastereoselective Reductive Difunctionalization of Alkenyl Amines
Zhao, Lei,Meng, Xiao,Zou, Yifeng,Zhao, Junsong,Wang, Lili,Zhang, Lanlan,Wang, Chao
, p. 8516 - 8521 (2021/10/25)
We report herein an intermolecular syn-arylalkylation and alkenylalkylation of alkenyl amines with two different organohalides (iodides and bromides) using Ni(II) catalyst. The cleavable bidentate quinolinamide is utilized after extensive directing group screening to enable olefin difunctionalization with high levels of regio-, chemo-, and diastereocontrol. This general and practical protocol is compatible with α- or β-substituted terminal alkenes and internal alkenes, providing rapid access to branched aliphatic amines bearing two skipped and vicinal stereocenters with high diastereoselectivities that would otherwise be difficult to synthesize.
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
supporting information, 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.
Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions
Kang, Ki-Tae,Park, Sang Hyun,Ryu, Do Hyun
, p. 6679 - 6683 (2019/09/12)
Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yi