29940-86-1Relevant academic research and scientific papers
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).
Synthesis of 4-Isoxazolines via Visible-Light Photoredox-Catalyzed [3 + 2] Cycloaddition of Oxaziridines with Alkynes
Jang, Gwang Seok,Lee, Junggeun,Seo, Jungseok,Woo, Sang Kook
supporting information, p. 6448 - 6451 (2017/12/08)
A method for [3 + 2] cycloaddition of oxaziridines with alkynes to form 4-isoxazolines via visible-light photoredox catalysis is described. This method is a greener, atom-economical reaction that tolerates various functional groups and provides good to excellent yield. Moreover, the cyclization products can be conveniently converted into tetrasubstituted allylic alcohols and enamines. A mechanistic study suggests that the reaction involves photoredox-catalyzed in situ generation of a nitrone from the oxaziridine by SET.
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.
The Reaction of α,β-Unsaturated Aldimines with Benzofuroxan
Devi, Purabi,Sandhu, Jagir S.
, p. 427 - 428 (2007/10/02)
Benzofuroxan reacts with imines derived from crotonaldehyde and cinnamaldehyde, to form 2-iminomethylquinoxaline 1,4-dioxides.
Organometallic Reactions of Conjugated Azomethines, IV. Catalytic Synthesis of Substituted Cyclohexanes from Butadiene and 1-Azadienes with ?-Allyl Palladium Complexes
Dieck, Heindirk tom,Mueller, Christiane,Haupt, Erhard T. K.,Bolze-Kuhrt, Doerte
, p. 853 - 859 (2007/10/02)
The reaction of dimeric ?-allyl palladium chloride with 1-azadienes 1 (R-N=CH-CH=CH-R') affords the mononuclear complexes (?-Allyl)Pd(L)Cl 2.Two independent intramolecular rotational motions are detected by NMR methods.These complexes (with R' = Aryl) rea
Halogenated Ketenes. 38. Cycloaddition of α,β-Unsaturated Imines with Ketenes To Yield Both β- and δ-Lactams
Brady, William T.,Shieh, C. H.
, p. 2499 - 2502 (2007/10/02)
The cycloaddition of various types of α,β-unsaturated imines with diphenyl- and dichloroketenes yields both (2 + 2) and (4 + 2) cycloaddition products, i. e., β-lactams and δ-lactams, respectively.The cycloaddition products are dependent upon substitution in the imine and the ketene.The δ-lactams derived from dichloroketene are easily dehydrochlorinated to the corresponding 2-pyridones.All of the results are consistent with a two-step cycloaddition process involving a dipolar intermediate.
