877264-44-3Relevant articles and documents
Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process
Steeds, Hannah G.,Knowles, Jonathan P.,Yu, Wai L.,Richardson, Jeffery,Cooper, Katie G.,Booker-Milburn, Kevin I.
, p. 14330 - 14334 (2020/10/12)
A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalysed approach is reported. Substrate scope is broad, allowing the incorporation of a wide range of functionality relevant to medicinal chemistry. Mechanistic studies demonstrate that the process occurs by acid-assisted C?N bond cleavage followed by β-hydride elimination to form a reactive diene, demonstrating that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represents a short and versatile route to the biologically important morphan scaffold.
Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C-N Bond Formation
Whyte, Andrew,Olson, Maxwell E.,Lautens, Mark
, p. 345 - 348 (2018/01/27)
A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and are present in bioactive molecules. This work highlights the challenge of competing intra- vs intermolecular palladium-catalyzed processes.
Intramolecular Pd-Catalyzed Arylation of 1-Amidosugars: A New Route to N-Glycosyl Quinolin-2-ones
Luong, Thi Thanh Huyen,Brion, Jean-Daniel,Lescop, Ewen,Alami, Mouad,Messaoudi, Samir
, p. 2126 - 2129 (2016/06/01)
The synthesis of N-glycosylated quinolin-2-ones via an intramolecular N-arylation of glycosylamides is reported. The coupling involves the use of only Pd(OAc)2 as the catalyst and nBu4NOAc as the base in 1,4-dioxane. This versatile approach allows the synthesis of various N-glycosylated quinolin-2-ones with exclusive α or β selectivity.