Montmorillonite K10 Catalyzed Nucleophilic Addition Reaction to Aldimines in Water

Akiyama, Takahiko; Matsuda, Keiichiro; Fuchibe, Kohei

doi:10.1055/s-2005-872162

Cited by 13 publications

(2 citation statements)

References 6 publications

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“…This reaction, carried out in water, was reported by Akiyama et al who used Montmorillonite K10, a clay that serves as solid acid catalyst (Table 6). 40 On treatment of aldimines with diethyl H-phosphonate in water in the presence of Montmorillonite K10 at room temperature for 24 hours, α-aminophosphonates were obtained in good yields (Table 6).…”

Section: Reactions In Watermentioning

confidence: 99%

Environmentally Benign Syntheses of α-Substituted Phosphonates: Preparation of α-Amino- and α-Hydroxyphosphonates in Water, in Ionic Liquids, and under Solvent-Free Conditions

Olszewski¹

2014

Synthesis

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Due to the interest in α-amino-and α-hydroxyphosphonates and their derivatives, which arises from the important biological activity exhibited by those compounds, the development of efficient protocols for their preparation is of great importance. In the last 10 years however, the chemistry of α-amino and α-hydroxyphosphonates has been witness to an explosion of research activities in the field of application of environmentally benign media. This fact can be partially attributed to the development of the field of green and sustainable chemistry and especially the implementation of green solvents that has a large potential to contribute to more sustainable processes in chemical, pharmaceutical and processing industries. This review provides the reader with an in-depth overview of advances in the synthesis of α-amino-and α-hydroxyphosphonates under eco-friendy conditions compiled into sections with respect to product type and reaction medium.

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Section: Reactions In Watermentioning

confidence: 99%

Environmentally Benign Syntheses of α-Substituted Phosphonates: Preparation of α-Amino- and α-Hydroxyphosphonates in Water, in Ionic Liquids, and under Solvent-Free Conditions

Olszewski¹

2014

Synthesis

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“…The synthetic potential of the method has been covered in a series of reviews [27,42,95]. During the last 10 years, direct hydrophosphonylation of imines has been widely used for the preparation of multifunctional a-aminophosphonic acids without the excessive use of protective groups [96][97][98][99][100][101][102][103]. Trialkyl phosphites were evaluated for addition reactions to a,b-unsaturated imines.…”

Section: Amidoalkylation In the Carbonyl Compound-amine-phosphite Thrmentioning

confidence: 99%

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Kukhar

Romanenko

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Aminophosphonic (and aminophosphinic) acids occupy a prominent position in the understanding of bioprocesses in living organisms and in the construction of new bioregulators -pharmaceuticals and agrochemicals. The so-called phosphorus analogs of the amino acids, aminophosphonic and aminophosphinic acids, are amino acid mimetics in which the carboxylic group is substituted by a phosphonic acid residue P(O)(OH) 2 or phosphinic acid group P(O)(OH)R. The replacement of the carboxylic group by a phosphonic or related moiety results in a number of important consequences: the central atom of a phosphonic acid function consists of an additional substituent that has a tetrahedral configuration in contrast to the planar carbonyl atom of carboxylic group. There are also significant differences in the acidity and steric bulk of these residues. The tetrahedral configuration of the pentavalent phosphorus atom mimics the transition state of the peptide bond cleavage reaction in some enzyme-substrate interactions that is used in the synthesis of new inhibitors. The hydrolytic stability of CÀP bonds is often used in order to prepare stable analogs of bioactive phosphates OÀP(O)(OH) 2 . In addition, aminophosphonic acids and their derivatives are important as metal-complexing agents, which have diagnostic and therapeutic applications, and as industrial chemicals in water treatment, metal extraction, or pollution control.Synthesis, and the chemical, physical, and biological properties of aminophosphonic acids and some directions for their practical application are presented in a number of reviews and book chapters. The most comprehensive account of the chemistry and biology of aminophosphonates and aminophosphinate which covers literature up to 2000 is presented in Kukhar and Hudson ([1] and references therein). Readers are referred to this reference for more detailed information concerning specific aspects of the chemistry and biological activity of aminophosphonic acid derivatives. The purpose of this chapter is to give an updated report on aminophosphonic acids as analogs of amino acids. Numerous heterocyclic compounds that contain both phosphonic and amino groups will not be covered in this report.

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