68718-89-8Relevant academic research and scientific papers
Phosphinoyl-aziridines as a new class of chiral catalysts for enantioselective Michael addition
Wujkowska, Zuzanna,Zawisza, Anna,Le?niak, Stanis?aw,Rachwalski, Micha?
, p. 230 - 235 (2018/12/05)
A series of new optically pure phosphine oxides containing chiral aziridine subunit were synthesized in good yields and applied as organocatalysts in asymmetric Michael reaction of various aliphatic aldehydes with β-nitrostyrene. The corresponding organoc
Aryl group - A leaving group in arylphosphine oxides
Stankevi?, Marek,Pisklak, Jolanta,W?odarczyk, Katarzyna
, p. 810 - 824 (2016/01/20)
The treatment of triphenylphosphine oxide with organometallic reagents leads to the substitution of up to three phenyl substituents with the incoming carbon nucleophile. The replacement of the phenyl/aryl group in tertiary diarylalkylphosphine oxides or even aryldialkylphosphine oxides was also observed. Naphthyl-substituted phosphine oxides undergo Michael-type addition at the naphthyl group when treated with organolithium reagent.
Efficient asymmetric synthesis of structurally diverse p-stereogenic phosphinamides for catalyst design
Han, Zhengxu S.,Zhang, Li,Xu, Yibo,Sieber, Joshua D.,Marsini, Maurice A.,Li, Zhibin,Reeves, Jonathan T.,Fandrick, Keith R.,Patel, Nitinchandra D.,Desrosiers, Jean-Nicolas,Qu, Bo,Chen, Anji,Rudzinski, Diandra M.,Samankumara, Lalith P.,Ma, Shengli,Grinberg, Nelu,Roschangar, Frank,Yee, Nathan K.,Wang, Guijun,Song, Jinhua J.,Senanayake, Chris H.
supporting information, p. 5474 - 5477 (2015/04/27)
The use of chiral phosphinamides is relatively unexplored because of the lack of a general method for the synthesis. Reported herein is the development of a general, efficient, and highly enantioselective method for the synthesis of structurally diverse P-stereogenic phosphinamides. The method relies on nucleophilic substitution of a chiral phosphinate derived from the versatile chiral phosphinyl transfer agent 1,3,2-benzoxazaphosphinine-2-oxide. These chiral phosphinamides were utilized for the first synthesis of readily tunable P-stereogenic Lewis base organocatalysts, which were used successfully for highly enantioselective catalysis.
The endocyclic restriction test: Investigation of the geometries of nucleophilic substitution at phosphorus(III) and phosphorus(V)
Tollefson, Michael B.,Li, James J.,Beak, Peter
, p. 9052 - 9061 (2007/10/03)
Double labeling has been used under the endocyclic restriction test to show that transfers of phosphorus from oxygen to carbon in the conversions of lithio phosphinite 1 to alkoxy phosphine 8, of lithio phosphinite 2 to alkoxy phosphine 9, of lithio phosphinate 3 to alkoxy phosphine oxide 10, and of lithio phosphinite borane 4 to alkoxy phosphine borane 11 proceed in an intramolecular fashion. The transfers of stereogenic phosphorus in the conversions of lithio phosphinite (R)-5 to alkoxy phosphine (R)-12, of lithio phosphinate (S)-6 to alkoxy phosphine oxide (S)-13, and of lithio phosphinite borane (R)-7 to alkoxy phosphine borane (R)-14 proceed with retention of stereochemistry at phosphorus. These results rule out the classic in-line S(N)2 pathway and the geometrically equivalent in-line addition-elimination pathway for these endocyclic transfers of phosphorus. The most likely pathway for these nucleophilic substitutions at phosphorus is initial apical nucleophilic attack followed by pseudorotation and elimination of the apical alkoxy leaving group.
Synthesis, Characterisation and Structure of Square-planar Palladium(II) Complexes with Phosphine-Pyridine Hybrid Ligands o-Ph2PC6H4CH2O(CH2)nC5H4N-2 (n = 1-3). Isolation of the First Transition-metal Complex with a trans-Chelating Bidentate PN Ligand
Tani, Kazuhide,Yabuta, Masami,Nakamura, Shingo,Yamagata, Tsuneaki
, p. 2781 - 2790 (2007/10/02)
The reaction of Na2 or with an equimolar amount of new bidentate hybrid ligands having a P and a N donor atom capable of trans chelation, o-Ph2PC6H4CH2O(CH2)nC5H4N-2 (n = 1-3), gave mainly the 1:1 complex PdCl2o-Ph2PC6H4CH2O(CH2)nC
