1421840-31-4Relevant academic research and scientific papers
Enantiodivergent Formation of C-P Bonds: Synthesis of P-Chiral Phosphines and Methylphosphonate Oligonucleotides
Baran, Phil S.,Eastgate, Martin D.,Knouse, Kyle W.,Padial, Natalia M.,Rivas-Bascón, Nazaret,Schmidt, Michael A.,Vantourout, Julien C.,Xu, Dongmin,Zheng, Bin
, (2020/03/30)
Phosphorus Incorporation (PI, abbreviated Π) reagents for the modular, scalable, and stereospecific synthesis of chiral phosphines and methylphosphonate nucleotides are reported. Synthesized from trans-limonene oxide, this reagent class displays an unexpected reactivity profile and enables access to chemical space distinct from that of the Phosphorus-Sulfur Incorporation reagents previously disclosed. Here, the adaptable phosphorus(V) scaffold enables sequential addition of carbon nucleophiles to produce a variety of enantiopure C-P building blocks. Addition of three carbon nucleophiles to Π, followed by stereospecific reduction, affords useful P-chiral phosphines; introduction instead of a single methyl group reveals the first stereospecific synthesis of methylphosphonate oligonucleotide precursors. While both Π enantiomers are available, only one isomer is required - the order of nucleophile addition controls the absolute stereochemistry of the final product through a unique enantiodivergent design.
Method for manufacturing a new dephosphorizing ligand homochiral (by machine translation)
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, (2016/10/10)
Disclosed are methods for making chiral phosphorus ligands including chiral phosphines, chiral phosphine oxides, phosphonamides, and aminophosphines. The chiral phosphorus ligands prepared by the methods of the invention are useful as components of chiral catalysts, e.g., transition metal complexes.
Efficient asymmetric synthesis of P -chiral phosphine oxides via properly designed and activated benzoxazaphosphinine-2-oxide agents
Han, Zhengxu S.,Goyal, Navneet,Herbage, Melissa A.,Sieber, Joshua D.,Qu, Bo,Xu, Yibo,Li, Zhibin,Reeves, Jonathan T.,Desrosiers, Jean-Nicolas,Ma, Shengli,Grinberg, Nelu,Lee, Heewon,Mangunuru, Hari P. R.,Zhang, Yongda,Krishnamurthy, Dhileep,Lu, Bruce Z.,Song, Jinhua J.,Wang, Guijun,Senanayake, Chris H.
, p. 2474 - 2477 (2013/03/28)
A general, efficient, and highly diastereoselective method for the synthesis of structurally and sterically diverse P-chiral phosphine oxides was developed. The method relies on sequential nucleophilic substitution on the versatile chiral phosphinyl transfer agent 1,3,2-benzoxazaphosphinine-2-oxide, which features enhanced and differentiated P-N and P-O bond reactivity toward nucleophiles. The reactivities of both bonds are fine-tuned to allow cleavage to occur even with sterically hindered nucleophiles under mild conditions.
