121197-53-3Relevant academic research and scientific papers
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 (1988)
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.
Enantioselective Mannich Reaction of Glycine Iminoesters with N-Phosphinoyl Imines: A Bifunctional Approach
Zhang, Changhui,Yang, Jiao,Zhou, Wenqiang,Tan, Qiuyuan,Yang, Zhao,He, Ling,Zhang, Min
supporting information, p. 8620 - 8624 (2019/11/03)
A bifunctional catalytic approach for the asymmetric Mannich reaction of glycine iminoesters with N-phosphinoyl imines has been developed. By the combination of metal catalysis and organocatalysis, the vicinal two stereogenic centers were efficiently constructed, affording a wide range of syn-diamino esters in high yields with excellent enantio- and diastereoselectivities (up to >99:1 dr, 99% ee).
Highly Diastereo- and Enantioselective Cu-Catalyzed Borylative Coupling of 1,3-Dienes and Aldimines
Jiang, Liyin,Cao, Peng,Wang, Min,Chen, Bin,Wang, Bing,Liao, Jian
supporting information, p. 13854 - 13858 (2016/10/26)
A Cu-catalyzed diastereo- and enantioselective borylative coupling reaction of 1,3-dienes with imines was realized. Branched homoallylic amines are readily prepared in a syn-selective manner with high regio-, diastereo- and enantioselectivity. Moreover, t
Enantioselective binaphthophosphepine-promoted [3+2] annulations of N-Ts- and N-DPP-imines with allenoates and 2-butynoates
Pinto, Nathalie,Fleury-Bregeot, Nicolas,Marinetti, Angela
body text, p. 146 - 151 (2009/07/05)
The use of binaphthophosphepine 1a as a catalyst for the [3+2] cyclisation between allenoates or 2-butynoates and imines was investigated. The effects of the imine protecting group on both the catalytic activity and enantioselectivity were determined by c
Synthesis of N-diphenylphosphinoylimines using the Kresze reaction
Lauzon, Caroline,Desrosiers, Jean-Nicolas,Charette, Andre B.
, p. 10579 - 10580 (2007/10/03)
The synthesis of N-diphenylphosphinoylimines involving the treatment of aldehydes with P,P-diphenyl N-sulfmylphosphoramidate (Ph2P(O)NSO) is described. The reagent is prepared from P,P-diphenylphosphinic amide, thionyl chloride, and imidazole.
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.
