Initially, the Atherton–Todd (AT) reaction was applied for the synthesis of phosphoramidates by reacting dialkyl phosphite with a primary amine in the presence of carbon tetrachloride. These reaction conditions were subsequently modified with the aim to optimize them and the reaction was extended to different nucleophiles. The mechanism of this reaction led to controversial reports over the past years and is adequately discussed. We also present the scope of the AT reaction. Finally, we investigate the AT reaction by means of exemplary applications, which mainly concern three topics. First, we discuss the activation of a phenol group as a phosphate which allows for subsequent transformations such as cross coupling and reduction. Next, we examine the AT reaction applied to produce fire retardant compounds. In the last section, we investigate the use of the AT reaction for the production of compounds employed for biological applications. The selected examples to illustrate the applications of the Atherton–Todd reaction mainly cover the past 15 years.

https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-10-117.pdf

Atherton–Todd reaction: mechanism, scope and applications

Disclosed herein are phosphorothioate nucleotide analogs, methods of synthesizing phosphorothioate nucleotide analogs and methods of treating diseases and/or conditions such as viral infections, cancer, and/or parasitic diseases with the phosphorothioate nucleotide analogs.

Substituted nucleotide analogs

In this chapter, new developments and main applications of vibrational circular dichroism (VCD) spectroscopy reported in the last 5 years are described. This includes the determinations of absolute configurations of chiral molecules, understanding solvent effects and modeling solvent–solute explicit hydrogen bonding networks using induced solvent chirality, studies of transition metal complexes and their peculiar and enormous intensity enhancements in VCD spectra, investigations of conformational preference of chiral ligands bound to gold nano particles, and two new advances in applying matrix isolation VCD spectroscopy to flexible, multi-conformational chiral molecules and complexes, and in development of femtosecond laser based VCD instruments for transient VCD monitoring. A brief review of the experimental techniques and theoretical methods is also given. The purpose of this chapter is to provide an up-to-date perspective on the capability of VCD to solve significant problems about chiral molecules in solution, in thin film states, or on surfaces.

Vibrational Circular Dichroism Spectroscopy of Chiral Molecules

N,O-Bis(trimethylsilyl)-α-amino acids (N,O-BTMS-AA), mediated by o-phenylene phosphorochloridate (PPC), could oligomerize into polypeptides. The mechanism might go through sequential steps, i.e., t...

Oligomerization of N,O-Bis(trimethylsilyl)-α-amino Acids into Peptides Mediated by o-Phenylene Phosphorochloridate

Time-Dependent Density Functional Response Theory for Electronic Chiroptical Properties of Chiral Molecules, by Jochen Autschbach, Lucia Nitsch-Velasquez, and Mark Rudolph * Recent Theoretical and Experimental Advances in the Electronic Circular Dichroisms of Planar Chiral Cyclophanes, by Yoshihisa Inoue and Tadashi Mori * G-C Content Independent Long-Range Charge Transfer Through DNA, by Kiyohiko Kawai and Tetsuro Majima * Transfer of Chirality for Memory and Separation, by Rosaria Lauceri, Alessandro D'Urso, Angela Mammana and Roberto Purrello * Vibrational Circular Dichroism Spectroscopy 4 of Chiral Molecules, by Guochun Yang and Yunjie Xu * Spin Selective Electron Transmission Through Monolayers of Chiral Molecules, by Ron Naaman and Zeev Vager * Chiral Control of Current Transfer in Molecules, by Vered Ben-Moshe, David N. Beratan, Abraham Nitzan and Spiros S. Skourtis * Spin-Polarized Electron Induced Asymmetric Reactions in Chiral Molecules, by Richard A. Rosenberg

Electronic and Magnetic Properties of Chiral Molecules and Supramolecular Architectures

Pentacoordinate spirobicyclic
2-phenoxy-1,3-phenylenedioxo-1,3,2-imino(alkyl)acetoxyphosphoranes are
synthesized through a new and efficient method whereby phosphorus
pentachloride is displaced stepwise by catechol, an
N,O-bis(trimethylsilyl)amino acid
and phenol (pathway A) or catechol, phenol and an
N,O-bis(trimethylsilyl)amino acid
(pathway B); this method has advantages of high yields, rapid reaction
times and easy operation, which might provide a new route for the
synthesis of other pentacoordinate phosphoranes.

New and efficient approach to the synthesis of pentacoordinate spirobicyclic phosphoranes

Synthesis of 2-Phenoxy-2,75-spiro[1,3,2-benzodioxaphosphole-2,2′-1,3,2-oxazophospholan]-5′-ones

Pentacoordinated phosphoranes containing valine or iso-leucine residue (2-phenyl-2,75-spiro[1,3,2-phenanthrodioxaphosphole-2,2′-1,3,2-oxazaphospholan]-5′-one) were synthesized through sequential two-step reactions, whereby the reaction products of phenyldichlorophosphine with N,O-bis(trimethylsilyl)valine or iso-leucine were followed by the addition of phenanthrenequione, and the crystals of 4a and 4b were obtained from benzene and hexane mixed solution. The x-ray structure of the crystals 4a and 4b revealed that they are distorted TBP, exhibiting RP absolute configuration. The 31P NMR spectra showed that the SP diastereomer could transfer into the other one RP that came out from the solution during crystallization. Correspondingly, when it was dissolved in solvents the RP diastereomer transferred into the other one SP, and the pair of diastereomers changed each other in solution at room temperature through a phosphonium carboxylate zwitterions intermediate. The work was supported by the National Natural ...

Synthesis, Crystal Structure, and Diastereomeric Transfer of Pentacoordinated Phosphoranes Containing Valine or Iso-Leucine Residue

Synthesis and Resolution of Dinucleotide(TpAZT) Phosphoramidates

Handle everyday research tasks with reliable, citation-backed results

Your personal Research Agent to handle research tasks with citation-backed results

Popular Tasks used by Researchers

How can I help with your research?

Meet SciSpace

Get more enhanced response by uploading the PDFs you want me to reference.

No relevant PDFs in your library

SciSpace is the AI research assistant for academics. Run systematic literature reviews on 280M+ papers, and write papers with cited sources. Trusted by 1M+ students, PhDs & researchers.

SciSpace | AI for Research

Analyze PDFs

Code & Manuscripts

Funding & Grants

Literature & Patents

Medical & Clinical Data

Systematic Review

Visualize & Present

Web & Data

Build a Google Scholar-like website for your research.

Build a website

Create charts and images for your research

Create a Chart

Write a paper for submission to a journal

Draft a manuscript

Patent Search

Design eye-catching scientific posters in minutes.

Scientific Poster Generation

Systematic Literature Review

One task is running at the moment. Your messages will be shown right after.

Drag and drop or click here to browse

Loved by <highlight>1 million+</highlight> researchers

Extract a list of specific topics and their sources from unstructured text

Topics

Compare and analyze relevant papers that matches with your search

Papers

Get insights from PDFs and bookmarked papers from your library

My library

Recent searches

Try searching for:

Catch AI-generated content in scholarly and non-scholarly content

{ai} Detector

Ai Writer

Get PDF Summaries, highlighted text explanations 

Chat with PDF

Effortlessly create in-text citations and bibliographies in APA and 2,500 other formats

Citation generator

Get explanations, summaries, and answers on academic papers

Ease up your research workflow with {scispace}'s cohort of exciting AI tools

Elevate your academic writing skills and convey your ideas the way you want

Paraphraser

Explore our range of reading and writing tools

Your file is being prepared and should be ready in a few minutes. If it's a large file, it might take a bit longer. You can close this window, and we'll email you the file when it's done.

You have reached a maximum limit of <strong>{limit}</strong> columns in the table. Remove at least <strong>1</strong> column to add or create another one.

Guang-Zhong Tu

Author Tools

Chat about Author