226723-83-7Relevant academic research and scientific papers
A cascade Aza-Cope/Aza-prins cyclization leading to piperidine derivatives
Nallasivam, Jothi L.,Fernandes, Rodney A.
, p. 2012 - 2022 (2015/03/18)
The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines has been explored. The use of glyoxalic acid as the carbonyl component afforded bicyclic structures as a result of the internal carboxylate anion trapping the intermediate cation. The unimolecular bis-, tris-, and tetrakis(homoallylamine)s efficiently delivered the appended bis-, tris- and tetrakis(piperidine-4-ol)s (tripod and crucifix shape, respectively) as new entities. The latter compound served as an excellent ligand in the Suzuki-Miyaura cross-coupling reaction to synthesize incrustoporin. The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines is described. A unimolecular tetrapiperidine derivative, which resulted from this strategy, was employed as a ligand in the Suzuki-Miyaura cross-coupling reaction of an α-iodobutenolide with an arylboronic acid in an efficient synthesis of incrustoporin and its analogues.
Short and efficient synthesis of fluorinated δ-lactams
Cogswell, Thomas J.,Donald, Craig S.,Long, De-Liang,Marquez, Rodolfo
, p. 717 - 728 (2015/02/19)
The diastereoselective synthesis of fluorinated δ-lactams has been achieved through an efficient five step process. The route can tolerate a range of functionalities, and provides a quick route for the generation of new fluorinated medicinal building blocks.
Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation
Pandiancherri, Shveta,Lupton, David W.
, p. 671 - 674 (2011/03/22)
Exposure of N-chloroamines to KOtBu or LDA, in the presence of PMDETA or HMPA, provides 2-azaallyl anions capable of π4s + π2s cycloaddition reactions with a range of olefins. Good yields were achieved with stabilised systems, however, they were more modest when accessing semi-stabilised 2-azaallyl anions. By modifying the reaction conditions, one-pot dehydrochlorination/allylation can also be achieved with a range of N-chloroamines.
Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids
Man, Chun Law,Tin, Wai Cheung,Wong, Kwok-Yin,Tak, Hang Chan
, p. 923 - 929 (2007/10/03)
(Chemical Equation Presented) Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium-(I) and allylindium(III) dibromide formed in the reaction, were studied by NMR spectroscopy to explain the selectivity.
