Asymmetric Synthesis of α-Methylphosphophenylalanine Derivatives Using Sulfinimine-Derived Enantiopure Aziridine-2-phosphonates

Davis, Franklin A.; McCoull, William; Titus, Donald D.

doi:10.1021/ol990855k

Cited by 46 publications

(26 citation statements)

References 20 publications

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“…48 However, three diastereoisomers were isolated: (S S ,1R,2R) in 56% yield and also an inseparable mixture of (S S ,1S,2R) and (S S ,1S,2S) (68 : 32) in 23% isolated yield. Very recently, the process has been extended by the same group to the preparation of b-amino-a-iodo phosphonates with very good yields.…”

Section: Synthesis Of B-amino-a-halogenated Phosphonatesmentioning

confidence: 98%

Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs

Palacios¹,

Alonso²,

Santos³

2005

Enantioselective Synthesis of Β-Amino Acids

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Section: Synthesis Of B-amino-a-halogenated Phosphonatesmentioning

confidence: 98%

Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs

Palacios¹,

Alonso²,

Santos³

2005

Enantioselective Synthesis of Β-Amino Acids

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“…Compounds 118 were generally regarded to have a half chair configuration based on the relationship between the vicinal coupling constants and dihedral angles (Scheme 40). 74 3-(Dimethylphosphino)piperidazine 121 can be synthesized via a Diels-Alder reaction of di-(-)-menthyl azodicarboxylate (120) and 1-trimethylsilyloxybutadiene (119) in the presence of trimethyl phosphite and a Lewis acid, as an inseparable mixture of diastereomers (Scheme 41). However, after hydrogenation of 121, the phosphonopiperidazines 122 and 123 can easily be separated by column chromatography.…”

Section: Scheme 37mentioning

confidence: 99%

Synthetic methods of cyclic α-aminophosphonic acids and their esters

Ali¹

2013

Arkivoc

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“…In a similar way, the mixture of 59 was converted into ( S )- 51d in 43% overall yield, after three steps (Scheme 15). 60…”

Section: Stereoselective Synthesis Of α-Aminophosphonic Acids and mentioning

confidence: 99%

An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives

2009

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An overview of all methodologies published during the last few years focused to the stereoselective (diastereoselective or enantioselective) synthesis of α-aminophosphonic acids and derivatives is reported. The procedures have been classified according a retrosynthetic strategy and taking into account the formation of each one of the bonds connected to the chiral centre. Keywordsα-Aminophosphonic acids; α-Aminophosphonates; Stereoselective Synthesis; Resolution; Chiral Pool Introducciónα-Aminoalkylphosphonic acids 1 are structurally analogous to α-amino acids 2, obtained by isosteric substitution of planar and less bulky carboxylic acid (CO 2 H) by a tetrahedral phosphonic acid functionality (PO 3 H 2 ). Several aminophosphonic, aminophosphinic and aminophosphonous acids have been isolated from various natural sources either as free amino acids or as constituents of more complex molecules. 1 Many natural and synthetic aminophosphonic acids, their phosphonate esters and short peptides incorporating this unit, exhibit a variety of biological properties. 2 Their diverse applications include enzyme inhibitors 3 such as synthase, 4 HIV protease, 5 rennin, 6 phosphatasa activity, 7 PTPases, 8 and potent antibiotics, 9 as antibacterial agents, 10 antiviral, 11 antifungal, 12 herbicides, 13 antitumor agents. 14 Their role for antibody generation is also well documented. 15 In addition, the incorporation of cyclic amino acids of medium ring size into key positions in peptide chains plays an important role, and constitutes the most prominent pathway to conformationally constrained peptidomimetics, a tool in modern drug discovery. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author ManuscriptIn addition, α-aminophosphonic acids and their monoalkyl esters are also of interest in hydrometallurgy in order to extract metals 17 and in diagnostic medicine as screening agents, once complexed with lanthanides and actinides. 18,19 It is well known that the biological activity of α-aminophosphonic acids and derivatives depends on the absolute configuration of the stereogenic α carbon to phosphorous. 20 For example, (R)-phospholeucine 3 is a more potent inhibitor of leucine aminopeptidase than the S enantiomer, 21 and (S,R)-alafosfalin 4 shows higher antibacterial activity against both Grampositive and Gram-negative microorganisms than the other three diastereoisomers. 22 In view of the different biological and chemical applications of the α-aminophosphonic acids and derivatives, in the last 35 years the development of suitable synthetic methodologies for their preparation in optically pure form has been a topic of great interest in several research groups. In this context, several protocols for efficient asymmetric synthesis of α-aminophosphonic acids and derivatives have emerged in the recent years and several reviews have been published. 23 Now we would like to report herein an update over stereoselective synthesis of α-aminophosphonic acids and derivatives from 1998-2007. The principal synthetic stra...

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Asymmetric Synthesis of α-Methylphosphophenylalanine Derivatives Using Sulfinimine-Derived Enantiopure Aziridine-2-phosphonates

Cited by 46 publications

References 20 publications

Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs

Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs

Synthetic methods of cyclic α-aminophosphonic acids and their esters

An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives

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