51584-30-6Relevant 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
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.
Reaction of Thiolo and Seleno Esters of Phosphorus Acids with Halogens. 1. Stereochemical and 31P NMR Studies of Reaction of S-Methyl tert-Butylphenylphosphinothiolate with Elemental Chlorine and Sulfuryl Chloride
Krawiecka, B.,Michalski, J.,Wojna-Tadeusiak, E.
, p. 4201 - 4208 (2007/10/02)
Reaction of S-methyl tert-butylphenylphosphinothiolate (4) with elemental chlorine and sulfuryl chloride involves chlorolysis of the P-S bond and formation of the tert-butylphenylphosphinochloridate 5.It is demonstrated here that the stereoselectivity of
The Proton Magnetic Resonance Spectra of Chiral Phosphinate Esters. Chemical Shift Non-equivalence of Enantiomers induced by Optically Active Phosphinothioic Acids
Harger, Martin J. P.
, p. 1505 - 1511 (2007/10/02)
The 1H n.m.r. spectrum of racemic methyl methylphenylphosphinate recorded in CCl4 solution in the presence of 1 mol. equiv. of (+)-(R)-phenyl-t-butylphosphinothioic acid or (-)-(S)-methylphenylphosphinothioic acid contains well separated P-m
