Enantiomeric O,O-dimenthyl α-iminotrifluoroethylphosphonates: Novel chiral building blocks in asymmetric synthesis of α-trifluoromethylated α-aminophosphonic acid derivatives

Rassukana, Yuliya V.; Stanko, Oleg V.; Onys’ko, P. P.

doi:10.1016/j.jfluchem.2019.01.007

Cited by 13 publications

(10 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, the use of proline ( I) as a chiral catalyst in the addition of acetone ( 33 ) gives α-aminophosphonate 34 in good yield and diastereoselectivity (86%, 1:30 dr). The authors also describe the addition of other nucleophiles to ketimines 32 , such as pyrroles 35 , indole ( 37 ), and nitromethane, to yield α-aminophosphonate derivatives 36 , 38 and 39 , although in these cases, they observe lower diastereoselectivities [ 37 ].…”

Section: Diastereoselective Synthesis Of Tetrasubstituted α-Aminophosphonic Acid Derivativesmentioning

confidence: 99%

Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives

et al. 2021

View full text Add to dashboard Cite

Due to their structural similarity with natural α-amino acids, α-aminophosphonic acid derivatives are known biologically active molecules. In view of the relevance of tetrasubstituted carbons in nature and medicine and the strong dependence of the biological activity of chiral molecules into their absolute configuration, the synthesis of α-aminophosphonates bearing tetrasubstituted carbons in an asymmetric fashion has grown in interest in the past few decades. In the following lines, the existing literatures for the synthesis of optically active tetrasubstituted α-aminophosphonates are summarized, comprising diastereoselective and enantioselective approaches.

show abstract

Section: Diastereoselective Synthesis Of Tetrasubstituted α-Aminophosphonic Acid Derivativesmentioning

confidence: 99%

Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Stanko and Rassukana proposed two other methods of obtaining non‐racemic 2,2,2‐trifluoro‐1‐aminoethanephosphonic acid 88 (Scheme 14, paths B and C) [104,105] . In one of these methods, the authors used an approach similar to that of Xiao et al ., to obtain chiral imidoyl chloride 96 .…”

Section: Antibacterial Amino Acid‐based Agentsmentioning

confidence: 99%

Amino Acid Based Antimicrobial Agents – Synthesis and Properties

2021

View full text Add to dashboard Cite

Structures of several dozen of known antibacterial, antifungal or antiprotozoal agents are based on the amino acid scaffold. In most of them, the amino acid skeleton is of a crucial importance for their antimicrobial activity, since very often they are structural analogs of amino acid intermediates of different microbial biosynthetic pathways. Particularly, some aminophosphonate or aminoboronate analogs of protein amino acids are effective enzyme inhibitors, as structural mimics of tetrahedral transition state intermediates. Synthesis of amino acid antimicrobials is a particular challenge, especially in terms of the need for enantioselective methods, including the asymmetric synthesis. All these issues are addressed in this review, summing up the current state‐of‐the‐art and presenting perspectives fur further progress.

show abstract

“…Onys'ko and coworkers reported earlier this year the synthesis of α-trifluoromethylated α-aminophosphonic acid derivatives (Rassukana et al, 2019). Optically pure (+)-or (-)-dimenthyl phosphite were reacted with trifluoroacetonitrile to yield O,O-dimenthyl α-iminotrifluoroethylphosphonates which were shown to be useful intermediates for the synthesis of a variety of substances, including chiral Ntosylated α-amino-β-nitrophosphonates via an aza-Henry reaction.…”

Section: Aminophosphonic and Amino Acid Derivativesmentioning

confidence: 99%

“…Their NMR spectrum showed that the more sterically hindered Z-configuration is the thermodynamically preferred one. The capability of producing and using unprotected iminophosphosphonates directly is very promising for future developments, because protecting group removal in functionalized phosphonates, particularly when electronwithdrawing groups are present, is often accompanied by cleavage of the C-P bond (Rassukana et al, 2019).…”

Section: Aminophosphonic and Amino Acid Derivativesmentioning

confidence: 99%

The Stereoselective Nitro-Mannich Reaction in the Synthesis of Active Pharmaceutical Ingredients and Other Biologically Active Compounds

2020

View full text Add to dashboard Cite

The nitro-Mannich (aza-Henry) reaction, in which a nitroalkane and an imine react to form a β-nitroamine, is a versatile tool for target-oriented synthesis. Although the first stereoselective reaction was developed only 20 years ago, and enantioselective and diastereoselective versions for the synthesis of non-racemic compounds soon after, there are nowadays a variety of reliable methods which can be used for the synthesis of APIs and other biologically active substances. Hence many anticancer drugs, antivirals, antimicrobials, enzyme inhibitors and many more substances, containing C-N bonds, have been synthesized using this reaction. Several transition metal complexes and organocatalysts were shown to be compatible with the presence of a wide range of functional groups in these molecules, and very high levels of asymmetric induction have been achieved in some cases. The reaction has also been applied in cascade processes. The structural diversity of the products, ranging from simple heterocycles or azabicycles to complex alkaloids, iminosugars, amino acids or diamino acids and phosphonates, shows the versatility of the nitro-Mannich reaction and its potential for future developments.

show abstract

Enantiomeric O,O-dimenthyl α-iminotrifluoroethylphosphonates: Novel chiral building blocks in asymmetric synthesis of α-trifluoromethylated α-aminophosphonic acid derivatives

Cited by 13 publications

References 28 publications

Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives

Asymmetric Synthesis of Tetrasubstituted α-Aminophosphonic Acid Derivatives

Amino Acid Based Antimicrobial Agents – Synthesis and Properties

The Stereoselective Nitro-Mannich Reaction in the Synthesis of Active Pharmaceutical Ingredients and Other Biologically Active Compounds

Contact Info

Product

Resources

About