77929-23-8Relevant academic research and scientific papers
Iridium-catalyzed enantioselective C-H borylation of diarylphosphinates
Song, Shu-Yong,Li, Yinwu,Ke, Zhuofeng,Xu, Senmiao
, p. 13445 - 13451 (2021/11/16)
P-stereogenic phosphorus compounds are a ubiquitous and critically important class of chiral ligands in asymmetric catalysis. Methods for catalytic asymmetric synthesis via a step- and atom-economic way are still very limited. We herein disclose a protocol of phosphinate-directed iridium-catalyzed enantioselective ortho-H borylation to construct P-stereogenic phosphorus compounds. A number of functional groups could be well tolerated to afford optically active diarylphosphinates with good to excellent enantioselectivities (up to 92% ee). We also demonstrate the synthetic utilities of the obtained borylated products, including the synthesis of precursors for chiral phosphine ligands.
A facile and practical preparation ofP-chiral phosphine oxides
Xu, Ronghua,Gao, Zhenhua,Yu, Yiteng,Tang, Yehua,Tian, Duanshuai,Chen, Tian,Chen, Yibing,Xu, Guangqing,Shi, Enxue,Tang, Wenjun
, p. 3335 - 3338 (2021/04/07)
A practical and cost-effective synthetic method ofP-chiral diarylalkyl, aryldialkyl, and triaryl phosphine oxides by using readily available chiral diphenyl-2-pyrrolidinemethanol as the auxiliary is developed. The long-standing racemization issue during s
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
supporting information, (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.
Chemo-, regio- and stereoselective conversion of P-chirogenic phosphorus borane complexes into their P=O or P=S derivatives
Uziel, Jacques,Darcel, Christophe,Moulin, Dominique,Bauduin, Christophe,Juge, Sylvain
, p. 1441 - 1449 (2007/10/03)
Chiral and achiral organophosphorus borane complexes are readily transformed into their corresponding phosphoryl or thiophosphoryl compounds in high yields using one-pot procedures with stereoselectivities reaching 100% in many cases. Both oxidation and sulfuration were performed under neutral or mild conditions and were applied to various organophosphorus borane complexes (phosphines, phosphinates, chlorophosphines, aminophosphines, etc.). In the case of the dissymmetric diphosphine or aminophosphine phosphinite ligands, the reaction of their diborane complexes proceeds regiospecifically to a single phosphorus group, affording the corresponding hybrid derivatives.
GRIGNARD REACTION OF 2-PHENYL-TETRAHYDROPYRROLO-1,3,2-OXAZAPHOSPHOLES, OBSERVATION OF THE STEREOSPECIFIC INVERSION OF CONFIGURATION
Koizumi, Toru,Yanada, Reiko (nee Ishizaka),Takagi, Hiroyasu,Hirai, Hajime,Yoshii, Eiichi
, p. 571 - 572 (2007/10/02)
Grignard reaction of bicyclic oxazaphospholes proceeded with inversion of configuration to provide chiral phosphinic esters of known absolute configurations.
