ChemInform Abstract: Direct Synthesis of α-Amino Amides from N-Alkyl Amines by the Copper-Catalyzed Oxidative Ugi-Type Reaction.

ChemInform ◽  
2012 ◽  
Vol 43 (23) ◽  
pp. no-no
Author(s):  
Xin Ye ◽  
Chunsong Xie ◽  
Rui Huang ◽  
Jinhua Liu
Keyword(s):  
Direct Synthesis ◽  
Type Reaction ◽  
Alkyl Amines ◽  
Amino Amides

Direct Synthesis of α-Amino Amides from N-Alkyl Amines by the Copper-Catalyzed Oxidative Ugi-Type Reaction

Synlett ◽  
2012 ◽  
Vol 23 (03) ◽  
pp. 409-412 ◽  
Author(s):  
Chunsong Xie ◽  
Jinhua Liu ◽  
Xin Ye ◽  
Rui Huang
Keyword(s):  
Direct Synthesis ◽  
Type Reaction ◽  
Alkyl Amines ◽  
Amino Amides

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.

A Synthetic and Computational Investigation into the Direct Synthesis of ?-Hydroxymethylated Enones from ?-Keto Phosphonates

2009 ◽  
Vol 62 (7) ◽  
pp. 720 ◽  
Author(s):  
Sarah J. Ryan ◽  
Christopher D. Thompson ◽  
David W. Lupton
Keyword(s):  
Reaction Mechanism ◽  
Direct Synthesis ◽  
Computational Studies ◽  
Computational Investigation ◽  
Type Reaction

The synthesis of a range of α-hydroxymethylated enones has been achieved using the Villiéras modification of the Horner–Wadsworth–Emmons (HWE) reaction. Scope, limitations, and mechanistic aspects of this reaction were investigated using a combination of synthetic and computational studies. These investigations support a Schlosser–Corey type reaction mechanism that is balanced between two pathways with the outcome influenced by the steric environment of the substrate.

A p-toluenesulfinic acid-catalyzed three-component Ugi-type reaction and its application for the synthesis of α-amino amides and amidines

2013 ◽  
Vol 54 (19) ◽  
pp. 2340-2343 ◽  
Author(s):  
Biswajit Saha ◽  
Brendan Frett ◽  
Yuanxiang Wang ◽  
Hong-yu Li
Keyword(s):  
Type Reaction ◽  
Acid Catalyzed ◽  
Amino Amides

Synthesis of enantiomerically-enriched N-aryl amino-amides via a Jocic-type reaction

2018 ◽  
Vol 59 (44) ◽  
pp. 3965-3968 ◽  
Author(s):  
Christian Hobson ◽  
Michael S. Perryman ◽  
Gavin Kirby ◽  
Guy J. Clarkson ◽  
David J. Fox
Keyword(s):  
Type Reaction ◽  
Amino Amides
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