scholarly journals Selective Pd-Catalyzed Monoarylation of Small Primary Alkyl Amines through Backbone-Modification in Ylide-Functionalized Phosphines (YPhos)

2020 ◽  
Vol 85 (22) ◽  
pp. 14674-14683
Author(s):  
Ilja Rodstein ◽  
Daniel Sowa Prendes ◽  
Leon Wickert ◽  
Maurice Paaßen ◽  
Viktoria H. Gessner
Keyword(s):  
Alkyl Amines ◽  
Small Primary ◽  
Backbone Modification

α-Ketophosphonates in the Synthesis of α-iminophosphonates

2020 ◽  
Vol 7 (2) ◽  
pp. 226-238
Author(s):  
Petro P. Ony`sko ◽  
Tetyana I. Chudakova ◽  
Vladimir V. Pirozhenko ◽  
Alexandr B. Rozhenko
Keyword(s):  
Bond Cleavage ◽  
Direct Synthesis ◽  
Equilibrium Mixture ◽  
Primary Amines ◽  
Alkyl Amines ◽  
Protic Solvents ◽  
Metallic Salts ◽  
Direct Preparation ◽  
Stage Synthesis ◽  
Aprotic Dipolar Solvent

The potentialities of condensation of α-ketophosphonates with primary amines for direct synthesis of α-iminophosphonates have been revealed. Diesters of α-ketophosphonic acids react with the primary amines by two competitive pathways: with a formation of α-iminophosphonates or a C-P bond cleavage resulting in a hydrogen phosphonate and an acylated amine. In many cases, the latter undesirable pathway is dominant, especially for more nucleophilic alkyl amines. Using metallic salts of α-ketophosphonates avoids the C-P bond cleavage, allowing direct preparation of α-phosphorylated imines by the reaction with primary amines. This strategy provides an atom economy single-stage synthesis of iminophosphonates – precursors of bio relevant phosphorus analogs of α-amino acids. Methyl sodium iminophosphonates, bearing aryl or heteryl substituents at the imino carbon atom exist in solutions at room temperature as an equilibrium mixture of Z- and E-isomers. A configuration of the C=N bond can be controlled by the solvent: changing the aprotic dipolar solvent DMSO-d6 by water or alcohols leads to the change from a predominant Z-isomer to almost an exclusive E-form. In contrast, diesters of the respective iminophosphonates exist in non-protic solvents predominantly in Econfiguration. The solvent effect on E-Z stereochemistry is demonstrated by DFT calculations.

scholarly journals Use of Backbone Modification To Enlarge the Spatiotemporal Diversity of Parathyroid Hormone Receptor-1 Signaling via Biased Agonism

2019 ◽  
Vol 141 (37) ◽  
pp. 14486-14490 ◽  
Author(s):  
Shi Liu ◽  
Frederic G. Jean-Alphonse ◽  
Alex D. White ◽  
Denise Wootten ◽  
Patrick M. Sexton ◽  
...  
Keyword(s):  
Parathyroid Hormone ◽  
Hormone Receptor ◽  
Parathyroid Hormone Receptor ◽  
Biased Agonism ◽  
Backbone Modification

Characterisation of alkyl amines at the water/air surface with the drop and bubble profile analysis tensiometry

2012 ◽  
Vol 372 (1) ◽  
pp. 202-206 ◽  
Author(s):  
Marion Winkelmann ◽  
Aliyar Javadi ◽  
Reinhard Miller ◽  
Heike Petra Schuchmann
Keyword(s):  
Profile Analysis ◽  
Alkyl Amines
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