Synthesis of (1S,2S)- and (1R,2R)-1-amino-2-methylcyclopropane-phosphonic acids from racemic methylcyclopropanone acetal

Tesson, Nicolas; Dorigneux, Benoist; Fadel, Antoine

doi:10.1016/s0957-4166(02)00609-2

Cited by 29 publications

(10 citation statements)

References 22 publications

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“…The key stage that determines the selectivity of the process Tesson et al [29] believe to be the nucleophilic attack of triethylphosphite on the iminium cation occurring prevailingly from the least sterically hindered side of the ring, opposite to the methyl substituent. The stereoinducing infl uence of the chiral substituent at the nitrogen atom is out of question for the use of (S)-or (R)-1-phenylethylamine gave the identical stereochemical result.…”

Section: Addition Of Phosphites To Cyclopropylideneiminium Cationsmentioning

confidence: 99%

“…The study of the bulk of the alkyl substituent in the three-membered ring on the direction of the attack of the triethylphosphite was continued in [29] on a series of racemic 2-alkyl-1-methoxy-1-trimethyl-silyloxycyclopropanes, and it was shown that in the case of the bulky tert-butyl substituent only trans-product was obtained, but the fraction of the trans-product in the series Me > Bn > Et > i-Pr decreased: 88 > 86 > 82 > 76%.…”

Section: Addition Of Phosphites To Cyclopropylideneiminium Cationsmentioning

confidence: 99%

“…The use instead of 1-phenylethylamine of aminoalcohol (R)-2-amino-2-phenylethanol resulted in the formation of a mixture (89 : 11) of diastereomers of cyclic aminophosphonates (each of them was a mixture of P*-epimers), which might be separated by chromatography [30] An interesting approach to the synthesis of optically pure (2-methyl-1-aminocyclopropyl)phosphonates from racemic acetal 2-methyl-1-methoxy-1-trimethylsilyloxycyclopropane is described in [29] based on the chromatographic separation of diastereomeric racemate of N-formylated trans-isomers of diethyl or diisopropyl (1S*,2S*,1'S)-[2-methyl-1-(1-phenylethylamino)cyclopropyl]phosphonates (Scheme 6).…”

Section: Addition Of Phosphites To Cyclopropylideneiminium Cationsmentioning

confidence: 99%

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Synthesis methods of (1-aminocyclopropyl)phosphonic acids

2011

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Section: Addition Of Phosphites To Cyclopropylideneiminium Cationsmentioning

confidence: 99%

Section: Addition Of Phosphites To Cyclopropylideneiminium Cationsmentioning

confidence: 99%

Section: Addition Of Phosphites To Cyclopropylideneiminium Cationsmentioning

confidence: 99%

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Synthesis methods of (1-aminocyclopropyl)phosphonic acids

2011

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“…For further details of this subject, readers are referred to the leading references cited in a monograph [27] and reviews [41,42]. In recent years, many new cyclic a-aminophosphonic acids have been prepared, such as a-aminocyclopropylphosphonic acids, as well as their cyclobutyl, cyclopentyl, and cyclohexyl analogs 13 [60,[79][80][81][82]. 4-Heterocyclohexyl phosphonates 14 and 3-heterocyclohexylphosphonates 15 were efficiently prepared from heterocyclic ketones via phosphite addition to iminium ions formed by in situ condensation of these ketones with benzylic amines [83].…”

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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“…Thus many cyclic a-aminophosphonic acids bearing the exocyclic amino group were prepared mostly in racemic series [10][11][12][13][14]. However, among a-aminophosphonates those containing nitrogen as a ring heteroatom are scarce.…”

Section: Introductionmentioning

confidence: 99%