30800-90-9Relevant articles and documents
Diversification of Unprotected Alicyclic Amines by C?H Bond Functionalization: Decarboxylative Alkylation of Transient Imines
Paul, Anirudra,Kim, Jae Hyun,Daniel, Scott D.,Seidel, Daniel
, p. 1625 - 1628 (2020/11/30)
Despite extensive efforts by many practitioners in the field, methods for the direct α-C?H bond functionalization of unprotected alicyclic amines remain rare. A new advance in this area utilizes N-lithiated alicyclic amines. These readily accessible intermediates are converted to transient imines through the action of a simple ketone oxidant, followed by alkylation with a β-ketoacid under mild conditions to provide valuable β-amino ketones with unprecedented ease. Regioselective α′-alkylation is achieved for substrates with existing α-substituents. The method is further applicable to the convenient one-pot synthesis of polycyclic dihydroquinolones through the incorporation of a SNAr step.
Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids
Lisnyak, Vladislav G.,Lynch-Colameta, Tessa,Snyder, Scott A.
supporting information, p. 15162 - 15166 (2018/10/26)
Even though there are dozens of biologically active 2-substituted and 2,6-disubstituted piperidines, only a limited number of approaches exist for their synthesis. Herein is described two Mannich-type additions to nitrones, one using β-ketoacids under catalyst-free conditions and another using methyl ketones in the presence of chiral thioureas, which can generate a broad array of such 2-substituted materials, as well as other ring variants, in the form of β-N-hydroxy-aminoketones. Both processes have broad scope, with the latter providing products with high enantioselectivity (up to 98 %). The combination of these methods, along with other critical steps, has enabled 8-step total syntheses of the 2,6-disubstituted piperidine alkaloids (?)-lobeline and (?)-sedinone.
Gold-catalysed synthesis of exocyclic vinylogous amides and β-amino ketones: A detailed study on the 5-exo/6-endo-dig selectivity, methodology and scope
Scarpi, Dina,Begliomini, Stefano,Prandi, Cristina,Oppedisano, Alberto,Deagostino, Annamaria,G?mez-Bengoa, Enrique,Fiser, Béla,Occhiato, Ernesto G.
, p. 3251 - 3265 (2015/05/20)
The gold(I)-catalysed reaction of N-Boc-protected 6-alkynyl-3,4-dihydro-2H-pyridines, which gives synthetically useful vinylogous amides (β-enaminones), has been studied in detail, in order to optimize the reaction conditions, enlarge the scope and gain i
