15286-49-4Relevant academic research and scientific papers
Synthesis of β-Phosphinolactams from Phosphenes and Imines
Fu, Xingyang,Li, Xinyao,Xu, Jiaxi
supporting information, p. 8733 - 8737 (2021/11/17)
Various cis-β-phosphinolactams are synthesized stereoselectively for the first time from imines and diazo(aryl)methyl(diaryl)phosphine oxides under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo the Wolf rearrangement to generate phosphenes. Imines nucleophilically attack the phosphenes followed by an intramolecular nucleophilic addition via less steric transition states to give final cis-β-phosphinolactams. C-Styrylimines generally give rise to β-phosphinolactams in higher yields than C-arylimines. The stereoselectivity and proposed mechanism are rationalized by DFT theoretical calculation.
Silylative Reductive Amination of α,β-Unsaturated Aldehydes: A Convenient Synthetic Route to β-Silylated Secondary Amines
Kim, Eunae,Park, Sehoon,Chang, Sukbok
supporting information, p. 5765 - 5769 (2018/03/28)
Described here is a reductive amination/hydrosilylation cascade of α,β-unsaturated aldehydes mediated by a Lewis acidic borane catalyst. The present reaction system provides an one-pot synthetic route towards β-silylated secondary amines that have not been accessible by other previous catalysis. Comparative 1H NMR studies on the silylative reduction of enimines revealed that steric bulkiness of primary amine reactants strongly affects both catalytic efficiency and regioselectivity. This strategy was applicable to a broad range of substrates and amenable to one-pot gram-scale synthesis. Moreover, a diastereoselective introduction of the β-silyl group was also found to be feasible (d.r. up to 71:29).
Modular access to vicinally functionalized allylic (thio)morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides
Braunstein, Hannah,Langevin, Spencer,Khim, Monique,Adamson, Jonathan,Hovenkotter, Katie,Kotlarz, Lindsey,Mansker, Brandon,Beng, Timothy K.
supporting information, p. 8864 - 8872 (2016/10/03)
A modular substrate-controlled hexannulation of inherently promiscuous 1,3-azadienes with hexacyclic anhydrides, which affords versatile vicinally functionalized allylic lactams, in high yields, regio- and stereoselectivities is described.
A modular approach to α,β-unsaturated N-aryl ketonitrones
Hood, Tyler S.,Bryan Huehls,Yang, Jiong
supporting information; experimental part, p. 4679 - 4682 (2012/09/05)
A modular approach to α,β-unsaturated N-aryl ketonitrones has been developed. Specifically, condensation of anilines and enals followed by alkylation of the resulting α,β-unsaturated imines provided N-allyl anilines, which were subjected to oxidation with
Asymmetric synthesis of α-aminophosphonates using the inexpensive chiral catalyst 1,1'-binaphthol phosphate
Xu, Weiming,Zhang, Sha,Yang, Song,Jin, Lin-Hong,Bhadury, Pinaki S.,Hu, De-Yu,Zhang, Yuping
experimental part, p. 5782 - 5796 (2010/12/19)
Asymmetric addition under mild conditions of dialkyl phosphites on aldimines derived from cinnamaldehyde catalyzed by the inexpensive chiral organocatalyst (R)-3,3'- [4-fluorophenyl]2-1,1'-binaphthol phosphate has been found effective to give n
