Aminophosphonates and aminophosphonic acids with tetrasubstituted stereogenic center: diastereoselective synthesis from cyclic ketimines

2019 ◽  
Vol 17 (31) ◽  
pp. 7352-7359 ◽  
Author(s):  
Jakub Iwanejko ◽  
Anna Brol ◽  
Bartłomiej M. Szyja ◽  
Marek Daszkiewicz ◽  
Elżbieta Wojaczyńska ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Aminophosphonic Acid ◽  
Aminophosphonic Acids ◽  
Stereogenic Center ◽  
Derivatives Of

Chiral tetrasubstituted aminophosphonic acid derivatives of hexahydroquinoxalin-2(1H)-one were synthesised via diastereoselective hydrophosphonylation of corresponding imines with tris(trimethylsilyl)phosphite as phosphorus nucleophile.

scholarly journals Highly Diastereoselective Construction of Carbon– Heteroatom Quaternary Stereogenic Centers in the Synthesis of Analogs of Bioactive Compounds: From Monofluorinated Epoxyalkylphosphonates to α-Fluoro-, β-, or γ-Amino Alcohol Derivatives of Alkylphosphonates

2021 ◽  
Vol 9 ◽  
Author(s):  
Magdalena Rapp ◽  
Klaudia Margas-Musielak ◽  
Patrycja Kaczmarek ◽  
Agnieszka Witkowska ◽  
Tomasz Cytlak ◽  
...  
Keyword(s):  
Phosphonic Acids ◽  
Important Amino Acid ◽  
Aminophosphonic Acids ◽  
Stereogenic Centers ◽  
Epoxide Opening ◽  
Tertiary Carbon ◽  
Stereogenic Center ◽  
Quaternary Stereogenic Centers ◽  
Derivatives Of ◽  
Methyl Phenyl

The synthesis of the stable surrogates of an important amino acid (R)-4-amino-3-hydroxybutyric acid (GABOB) such as substituted hydroxy aminophosphonic acids bearing a quaternary stereogenic center is presented. Highly diastereoselective formations of fluorinated spiroepoxy alkylphosphonate or related tertiary carbon-containing oxiranes from β-keto phosphonates possessing methyl, phenyl, or cyclohexenyl substituents, are reported. Stereoselective acid-promoted epoxide opening by bromide or azide followed by reduction/protection afforded tertiary bromides or N-Boc derivatives of β-amino-γ-hydroxy alkylphosphonates in most cases, while the reactions of oxiranes with different amines yielded their β-hydroxy-γ-amino regioisomers. Surprisingly, during the synthesis of amino phosphonic acids, we observe that the acid-induced rearrangement proceeded in a high diastereospecific manner, leading finally to substituted β-hydroxy-γ-aminoalkylphosphonic acids.

ChemInform Abstract: Asymmetric Diastereoselective Synthesis of Spirocyclopropane Derivatives of Oxindole.

ChemInform ◽  
2015 ◽  
Vol 46 (6) ◽  
pp. no-no
Author(s):  
Maksim Oseka ◽  
Artur Noole ◽  
Sergei Zari ◽  
Mario Oeeren ◽  
Ivar Jaerving ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Derivatives Of

Diastereoselective synthesis of α-aminoalkylphosphonic acid derivatives of Betti base

2014 ◽  
Vol 63 (6) ◽  
pp. 1390-1394 ◽  
Author(s):  
K. E. Metlushka ◽  
D. N. Sadkova ◽  
L. N. Shaimardanova ◽  
K. A. Nikitina ◽  
A. I. Tufatullin ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Betti Base ◽  
Aminoalkylphosphonic Acid ◽  
Derivatives Of

Diastereoselective synthesis of spiro derivatives of 3-substituted 2,3,4,4a,5,6-hexahydro-1H-benzo[c]quinolizines

2009 ◽  
Vol 45 (5) ◽  
pp. 743-754 ◽  
Author(s):  
T. V. Glukhareva ◽  
E. V. Deeva ◽  
A. Yu. Platonova ◽  
I. V. Geide ◽  
M. I. Kodess ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Spiro Derivatives ◽  
Derivatives Of

Asymmetric Diastereoselective Synthesis of Spirocyclopropane Derivatives of Oxindole

2014 ◽  
Vol 2014 (17) ◽  
pp. 3599-3606 ◽  
Author(s):  
Maksim Ošeka ◽  
Artur Noole ◽  
Sergei Žari ◽  
Mario Öeren ◽  
Ivar Järving ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Derivatives Of
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