Direct Access to Enantiomerically Enriched α-Amino Phosphonic Acid Derivatives by Organocatalytic Asymmetric Hydrophosphonylation of Imines

Pettersen, Daniel; Marcolini, Mauro; Bernardi, Luca; Fini, Francesco; Herrera, Raquel P.; Sgarzani, Valentina; Ricci, Alfredo

doi:10.1021/jo060708h

Cited by 142 publications

(53 citation statements)

References 21 publications

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“…20 Chemical shifts for aromatic protons of the title compounds (3a-l) appeared as complex multiplet at δ 6.34 -8.44. 24 The GC mass spectra of 3a-l agreed with the proposed structures.…”

Section: Resultssupporting

confidence: 64%

Microwave Assisted One-pot Synthesis of Novel α-Aminophosphonates and heir Biological Activity

Rao¹,

Rao²,

Rao³

et al. 2010

Bulletin of the Korean Chemical Society

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A simple and efficient synthesis of various α-aminophosphonates (3a-l) by the reaction of substituted aromatic/heterocyclic aldehydes, 2-amino-6-methoxy-benzothiazole and dibutyl/diphenyl phosphites under microwave irradiation without catalyst was accomplished. The phosphonates were characterized by elemental analysis, IR, 1 H, 13 C-and 31 P-NMR spectra. They showed promising antimicrobial, anti-oxidant activities depending on the nature of bioactive groups at the α-carbon.

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“…20 Chemical shifts for aromatic protons of the title compounds (3a-l) appeared as complex multiplet at δ 6.34 -8.44. 24 The GC mass spectra of 3a-l agreed with the proposed structures.…”

Section: Resultssupporting

confidence: 64%

Microwave Assisted One-pot Synthesis of Novel α-Aminophosphonates and heir Biological Activity

Rao¹,

Rao²,

Rao³

et al. 2010

Bulletin of the Korean Chemical Society

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“…The N-H proton signal appeared as singlet. The methylene protons of P-OCH 2 CH 3 showed a multiplet and methyl protons of P-OCH 2 CH 3 showed a triplet in the region of δ 3.55-3.99 and δ 1.05-1.38 respectively 16 . 31 Chem Sci Trans., 2013, 2(S1), S167-S172 S169 …”

Section: Resultsmentioning

confidence: 93%

One Pot Synthesis, Characterisation and Antimicrobial Activity of α- Amino Phosphonates

2013

Chem Sci Trans

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Abstract:The synthesis of some new α-amino phosphonates (4a-j) was accomplished by one pot reaction of equimolar quantities of 2-amino-4-chloro-5-nitro phenol (1), aromatic aldehydes (2a-j) and diethyl / dimethylphosphite (3) in dry tetrahydrofuran at reflux condition via Kabachnik -fields reaction in high yields. All the synthesized compounds were characterised by IR, 1 H, 13 C, 31 P NMR and examined for their antimicrobial activity and found to possess good activity.

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“…For example, by using 10 mol% of quinine as the catalyst in the enantioselective addition of dimethyl phosphite to N-Boc-protected imines, a-aminophosphonates 44 have been obtained in moderate to good yields and with up to 94% e.e. (Scheme 5.22) [126]. …”

Section: Rchomentioning

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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Direct Access to Enantiomerically Enriched α-Amino Phosphonic Acid Derivatives by Organocatalytic Asymmetric Hydrophosphonylation of Imines

Cited by 142 publications

References 21 publications

Microwave Assisted One-pot Synthesis of Novel α-Aminophosphonates and heir Biological Activity

Microwave Assisted One-pot Synthesis of Novel α-Aminophosphonates and heir Biological Activity

One Pot Synthesis, Characterisation and Antimicrobial Activity of α- Amino Phosphonates

Chemistry of Aminophosphonic Acids and Phosphonopeptides

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