260997-38-4Relevant academic research and scientific papers
The Generation of Difluoroketenimine and Its Application in the Synthesis of α,α-Difluoro-β-amino Amides
Zhang, Rui,Zhang, Zhikun,Zhou, Qi,Yu, Lefei,Wang, Jianbo
supporting information, p. 5744 - 5748 (2019/03/28)
Fluorine-containing β-amino acids and their derivatives have attracted significant attention due to their importance in life sciences. Herein the previously unknown difluoroketenimine, the analogue of the elusive difluoroketene, has been generated by the
Visible-light, iodine-promoted formation of n-sulfonyl imines and n-alkylsulfonamides from aldehydes and hypervalent iodine reagents
Hopkins, Megan D,Brandeburg, Zachary C.,Hanson, Andrew J.,Lamar, Angus A
, (2018/08/04)
Alternative synthetic methodology for the direct installation of sulfonamide functionality is a highly desirable goal within the domain of drug discovery and development. The formation of synthetically valuable N-sulfonyl imines from a range of aldehydes,
Formation of: N -sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes
Hopkins, Megan D.,Scott, Kristina A.,Demier, Brettany C.,Morgan, Heather R.,Macgruder, Jesse A.,Lamar, Angus A.
, p. 9209 - 9216 (2017/11/14)
A mild and operationally convenient formation of synthetically valuable N-sulfonyl imines from a range of aryl aldehydes by reaction with iminoiodinanes (PhINZ) and I2 has been developed. According to mechanistic experiments described within, the reaction is speculated to proceed through an unconventional light-promoted, N-centered radical (NCR) pathway involving a N,N-diiodosulfonamide reactive species. This method not only provides a new pathway toward the production of activated imines, but also serves as an example of a non-traditional means of carbonyl activation via an NCR species.
Highly Enantioselective Ferrocenyl Palladacycle-Acetate Catalysed Arylation of Aldimines and Ketimines with Arylboroxines
Schrapel, Carmen,Frey, Wolfgang,Garnier, Delphine,Peters, René
supporting information, p. 2448 - 2460 (2017/02/23)
Benzylic N-substituted stereocenters constitute a frequent structural motif in drugs. Their highly enantioselective generation is hence of technical importance. An attractive strategy is the arylation of imines with organoboron reagents. Chiral Rh complexes have reached a high level of productivity for this reaction type. In this article we describe that an electron rich PdIIcatalyst also performs well in the arylation of aldimines, comparable to the best Rh catalysts. The ferrocenyl palladacycle-acetate catalyst allows for a broad substrate scope and very high enantioselectivities. Commonly observed side reactions like aryl–aryl homocouplings and imine hydrolysis could be blocked. Mechanistic studies implicate that a) the acetate ligand is crucial for transmetallation, b) the active catalyst is most likely a palladacycle-OAc monomer, c) the rate limiting step is probably the product release. By added KOAc the arylation could also be applied to ketimines.
Exogenous-Base-Free Palladacycle-Catalyzed Highly Enantioselective Arylation of Imines with Arylboroxines
Schrapel, Carmen,Peters, Ren
supporting information, p. 10289 - 10293 (2015/09/01)
Enantiomerically pure benzylic amines are important for the development of new drugs. A readily accessible planar-chiral ferrocene-derived palladacycle is shown to be a highly efficient catalyst for the formation of N-substituted benzylic stereocenters; t
Cycloadditions of N-sulfonyl nitrones generated by Lewis acid catalyzed rearrangement of oxaziridines
Partridge, Katherine M.,Anzovino, Mary E.,Yoon, Tehshik P.
, p. 2920 - 2921 (2008/10/09)
We have developed cycloaddition reactions of novel, electron-deficient N-nosyl nitrones that arise from the titanium(IV)-catalyzed rearrangement of the corresponding N-nosyl oxaziridines. A diverse range of styrenes and oxaziridines react smoothly in this
Highly enantioselective aza-Baylis-Hillman reactions catalyzed by chiral thiourea derivatives
Raheem, Izzat T.,Jacobsen, Eric N.
, p. 1701 - 1708 (2007/10/03)
We report the discovery of asymmetric aza-Baylis-Hillman (ABH) reactions of N-p-nitrobenzenesulfonylimines with methyl acrylate catalyzed by chiral thiourea derivatives. A series of aromatic imines was found to undergo coupling with methyl acrylate with u
C2-symmetric bicyclo[3.3.1]nonadiene as a chiral ligand for rhodium-catalyzed asymmetric arylation of N-(4-nitrobenzenesulfonyl)arylimines
Otomaru, Yusuke,Tokunaga, Norihito,Shintani, Ryo,Hayashi, Tamio
, p. 307 - 310 (2007/10/03)
(Chemical Equation Presented) Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99percent ee) was realized by use of a new C 2-symmetric diene ligand, (1R,5R)-2,6-diphenylbicyclo[3.3.1]nona-2,6- diene (Ph-bnd*), for th
