α-(Ferrocenyl)-aminomethanephosphonous acids. First synthesis and preparation of their esters with cholesterol and adenosine

Lewkowski, J.; Rzeźniczak, Monika; Skowroński, R.

doi:10.1016/j.jorganchem.2004.02.025

Cited by 9 publications

(3 citation statements)

References 22 publications

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“…He is the author of more than 400 papers, including several reviews. Additionally, Lewkowski et al 10 carried out the condensation reaction of α-amino-H-phosphinic acid 5g, with cholesterol and O,O′-i-propylideneadenosine in the presence of dicyclohexylcarbodiimide (DCC) in CH 2 Cl 2 , obtaining the αamino-H-phosphinates 6a,b exclusively as two diastereoisomers in a 2:1 ratio in both cases. This suggests that for each diastereoisomeric form of the α-amino-H-phosphinic acid 5g, the newly formed chiral center on the phosphorus atom occurs with very high stereoselectivity (Scheme 3).…”

Section: Chiral Imine Compoundsmentioning

confidence: 99%

Stereoselective Synthesis of α-Amino-H-phosphinic Acids and Derivatives

et al. 2016

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α-Amino-H-phosphinic acids and derivatives are an important group of compounds of synthetic and pharmacological interest, and particular attention has been dedicated toward their stereoselective synthesis in recent years. While some of these compounds show activity by themselves, they are also valuable starting materials in the synthesis of phosphinic bioisosteres of natural peptides, where the hydrolyzable bond is substituted by a phosphinic functionality that mimics the transition state of peptide hydrolysis, thus acting as efficient enzyme inhibitors in which the molecular stereochemistry is demonstrated to be critical. This review summarizes the latest developments on the asymmetric synthesis of acyclic and phosphacyclic α-amino-Hphosphinic acids and derivatives following an order according to the strategy used; in addition, some implications in medicinal chemistry are disclosed. 1 Introduction 2 Stereoselective Synthesis of Acyclic α-Amino-H-phosphinic Acids and Derivatives 2.1 Stereoselective C-P Bond Formation (Addition of Phosphorus Compounds to Imines) 2.1.1 Chiral Imine Compounds 2.2 Stereoselective C-P Bond Formation (One-Pot, Three-Component Reaction) 2.2.1 Chiral Amino Compounds 2.3 Stereoselective CC Bond Formation 2.3.1 Diastereoselective Alkylations 2.4 Resolution Methodologies 2.5 Conversion from Chiral α-Aminophosphonates 3 Synthesis of Phosphacyclic α-Amino-H-phosphinates 3.1 1,4,2-Oxazaphosphacycles 4 Concluding Remarks

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Section: Chiral Imine Compoundsmentioning

confidence: 99%

Stereoselective Synthesis of α-Amino-H-phosphinic Acids and Derivatives

et al. 2016

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“…While the 20,22-monoester 32 was the predominant product in the presence of reagent 9, the use of boronic acid 10 led to a mixture of ester 33 and diester 34. α-(Ferrocenyl)-aminomethanephosphonous acid derivatives were prepared (Scheme 1) to connect the ferrocenyl group and the steroid skeleton with the help of aminophosphonous acid, often found in biologically-active compounds. 36 Esters 35a-c were obtained as mixtures of four diastereoisomers, which were clearly visible in 31 P NMR spectra as four well-separated signals. The ratio of diastereoisomers varied from 2:2:3:3 in the case of N-diphenylmethyl derivative 35c to even 1:1:6:6 in the case of 35b, while the use of N-(R)-α-methylbenzylamino(ferrocenyl) methane phosphonous acid as the acylating agent led to the formation of two diastereoisomers of 35d in a 1:2 ratio.…”

Section: Introductionmentioning

confidence: 99%

Synthetic methods towards steroid-ferrocene conjugates

Skoda‐Földes¹,

Váradi²

2022

Arkivoc

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Steroid-ferrocene conjugates, in which a steroid skeleton is connected directly or via a linker group to the ferrocene moiety, have a broad scope of possible applications in medicinal or analytical chemistry as well as in materials science. They may integrate or even enhance many of the attractive properties of the components. Reactive functional groups of steroids and the ease in the conversion of ferrocene via aromatic substitution reactions offer a wide range of possibilities to attach the two skeletons to each other. This review summarizes the diverse methodologies used in the synthesis of conjugates, including classical organic reactions as well as the application of organometallic reagents and transition-metal catalyzed reactions.

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“…Diastereoselectivity of reported reactions varied from 2:1 to 9:1 of diastereoisomeric ratio. Obtained diastereoisomeric aminophosphonates should be separated by chromatographic methods and then undergo hydrolysis to obtain free acids, which influenced badly substituents-such conditions are suitable neither for a furan ring [6][7][8][9][10][11] nor for a ferrocene moiety [12,13]. To avoid this problem, 100% diastereoselective addition of hypophosphorous acid to chiral Schiff bases has been applied [14][15][16][17][18] and formed aminophosphonous acids were subsequently oxidized to give aminophosphonic systems.…”

Section: Introductionmentioning

confidence: 99%