98837-39-9Relevant academic research and scientific papers
Iron-Catalyzed Asymmetric Nitro-Mannich Reaction
Dudek, Agata,Mlynarski, Jacek
, p. 11218 - 11224 (2017/10/27)
The first enantioselective addition of nitroalkanes to imines (nitro-Mannich reaction), mediated by an iron(II) catalyst assembled by a hindered hydroxyethyl-pybox ligand, is described. This valuable carbon-carbon bond-forming reaction proceeds smoothly at room temperature to afford enantioenriched β-nitro amines in good yields and high enantioselectivity, up to 98% with unprecedentedly low iron catalyst loading (5 mol %).
(Thiolan-2-yl)diphenylmethyl benzyl ether/N,N′-diarylurea cocatalyzed asymmetric aziridination of cinnamyl bromide and aryl aldimine
Wang, Shang-Hua,Chein, Rong-Jie
supporting information, p. 2607 - 2615 (2016/05/11)
A dual catalyst system using THT-based chiral sulfide 2a and H-bond donor 10a was developed for the asymmetric imino Corey-Chaykovsky reaction. Under the optimum reaction conditions, cinnamyl bromide reacted with a wide scope of N-diphenylphosphinic aldim
Nucleophilic addition of TMSCCl3 to N-phosphinoyl benzaldimines: A route to N-phosphinoyl-α-(trichloromethyl)benzylamines
Wahl, Benoit,Cabré, Albert,Woodward, Simon,Lewis, William
, p. 5829 - 5831 (2015/02/02)
Nucleophilic addition of readily available TMSCCl3 to N-phosphinoyl benzaldimines allows preparation of N-phosphinoyl-α-(trichloromethyl)benzylamines. Typically, the reaction in THF at room temperature using tetrabutylammonium difluorotriphenylsilicate (TBAT) as a catalytic promoter, afforded very good yields (65-95% range) for most derivatives within 1 h at room temperature.
Enantioselective synthesis of diaryl aziridines using tetrahydrothiophene- based chiral sulfides as organocatalysts
Huang, Meng-Ting,Wu, Hsin-Yi,Chein, Rong-Jie
supporting information, p. 1101 - 1103 (2014/01/17)
This work describes catalytic and asymmetric aziridinations (15 examples, 95-98% ee) of benzyl bromide and imines via the imino Corey-Chaykovsky reaction using (thiolan-2-yl)diarylmethanol benzyl ether as an organocatalyst. The catalyst and analogues thereof were prepared through an expeditious and efficient synthetic route featuring a double nucleophilic substitution and Shi epoxidation as key steps.
Stereoselective synthesis of α-silylamines by the direct addition of silyl anions to activated imines
Ballweg, David M.,Miller, Rebecca C.,Gray, Danielle L.,Scheidt, Karl A.
, p. 1403 - 1406 (2007/10/03)
(Chemical Equation Presented) A highly efficient stereoselective synthesis of unusual α-silylamines via a direct silyl anion addition reaction is reported. This approach is convergent and avoids any problematic aza-Brook shifts of the anionic intermediate
The titanium tetrachloride induced synthesis of N-phosphinoylimines and N-sulphonylimines directly from aromatic aldehydes
Jennings, W. Brian,Lovely, Carl J.
, p. 5561 - 5568 (2007/10/02)
The reaction of phosphinic amides or sulphonamides with an aromatic aldehyde in the presence of titanium tetrachloride and triethylamine provides a simple, one-step preparation of N-phosphinoylimines (5a-e) and N-sulphonylimines (7a-g). The extension of this reaction to ketones failed to give the desired imines, the aldol condensation products were obtained instead. The reaction of (+)-camphor with phosphinic amides or sulphonamides in refluxing toluene in the presence of titanium tetrachloride and triethylamine affords the (-)-camphorphosphinoyl- and (-)-camphorsulphonylimines in moderate yield.
Imines and Derivatives. Part 20. N-Phosphinoyloxaziridines: Synthesis and Structural Characterisation by Nuclear Magnetic Resonance Spectroscopy and a Crystal Structure of 3-(4-Chlorophenyl)-2-(diphenylphosphinoyl)oxaziridine
Boyd, Derek R.,Malone, John F.,McGuckin, M. Rosaleen,Jennings, W. Brian,Rutherford, Mark,Saket, Barahman M.
, p. 1145 - 1150 (2007/10/02)
The preparation of a new class of oxaziridines containing an N-phosphinoyl group is described.The compounds were obtained by peroxyacid oxidation of N-phosphinoyl imines under basic or neutral conditions, and characterised by n.m.r. spectroscopy.Revelant 2JPC, 3JPH, and 1JCH coupling constants are reported.An X-ray structure analysis of the title compound establishes that the 2-diphenylphosphinoyl group is trans to the 3-aryl ring.The P-N bond length (1.76 Angstroem) is abnormally high for an aminophosphorus(v) compound and the nitrogen atom is pyramidal (ΣN=280 deg).This geometry is interpreted in terms of an unusually low degree of ?-bonding between nitrogen and phosphorus due to the high s-character of the nitrogen lone pair.
AN EFFICIENT METHOD FOR THE PREPARATION OF N-PHOSPHINOYL AND N-SULPHONYL IMINES DIRECTLY FROM AROMATIC ALDEHYDES
Jennings, W. Brian,Lovely, Carl J.
, p. 3725 - 3728 (2007/10/02)
Reaction of phosphinamides and sulphonamides with aromatic aldehydes at 0 deg C in the presence of titanium tetrachloride and triethylamine provides a simple one-step preparation of N-phosphinoyl and N-sulphonyl imines.
N-Phosphinoyl Oxaziridines; A New Class of Oxaziridines
Boyd, Derek R.,Jennings, W. Brian,McGuckin, Rosaleen M.,Rutherford, Mark,Saket, Barahman M.
, p. 582 - 583 (2007/10/02)
Novel stable N-phosphionoyl oxaziridines have been prepared and characterised by n.m.r. and mass spectrometry; they function as oxidants towards phospines, sulphides, and alkenes
