356762-89-5Relevant articles and documents
HFIP-mediated 2-aza-Cope rearrangement: Metal-free synthesis of α-substituted homoallylamines at ambient temperature
Gadde, Karthik,Maes, Bert U. W.,Abbaspour Tehrani, Kourosch
supporting information, p. 4067 - 4075 (2021/05/19)
An efficient metal-free strategy for the synthesis of α-substituted homoallylamine derivatives has been developed via a 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-promoted 2-aza-Cope rearrangement of aldimines, generated in situ by condensation of aldehydes with easily accessible 1,1-diphenylhomoallylamines. This reaction provides rapid access to α-substituted homoallylamines with excellent functional group tolerance and yields. The reaction takes place at room temperature and no chromatographic purification is required for product isolation. The synthetic utility of the current method is further demonstrated by the transformation of the obtained benzophenone ketimines into N-unprotected homoallylamines, an α-amino alcohol and an α-amino amide. This journal is
Primary α-tertiary amine synthesis via α-C-H functionalization
Vasu, Dhananjayan,Fuentes de Arriba, Angel L.,Leitch, Jamie A.,De Gombert, Antoine,Dixon, Darren J.
, p. 3401 - 3407 (2019/03/21)
A quinone-mediated general synthetic platform for the construction of primary α-tertiary amines from abundant primary α-branched amine starting materials is described. This procedure pivots on the efficient in situ generation of reactive ketimine intermediates and subsequent reaction with carbon-centered nucleophiles such as organomagnesium and organolithium reagents, and TMSCN, creating quaternary centers. Furthermore, extension to reverse polarity photoredox catalysis enables reactivity with electrophiles, via a nucleophilic α-amino radical intermediate. This efficient, broadly applicable and scalable amine-to-amine synthetic platform was successfully applied to library and API synthesis and in the functionalization of drug molecules.
Alkylative Amination of Biogenic Furans through Imine-to-Azaallyl Anion Umpolung
Blume, Fabian,Albeiruty, Mhd Haitham,Deska, Jan
, p. 2093 - 2099 (2015/07/15)
Starting from biogenic furfurals, an operationally simple and scalable condensation-umpolung-alkylation protocol was employed in the synthesis of racemic furfurylamines. Subsequent enzymatic kinetic resolution by ω-transaminase or lipase biocatalysts allows for the preparation of functionalized heterocyclic building blocks from biogenic base chemicals in optically pure form.
