Zur Reaktion von Aminosäuren mit Formaldehyd und sekundären Phosphinen

Kellner, K.; Hanke, W.; Tzschach, A.

doi:10.1002/zfch.19840240518

Cited by 13 publications

(5 citation statements)

References 3 publications

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“…The 2,2‐bis‐phosphanylethyl amino acid derivatives XI were made by addition of amino acid derivatives to (Ph 2 P) 2 C=CH 2 . Acyclic and heterocyclic phosphanylmethyl amino acids or esters VIII ,, IX , X ,, phosphabenzylimino mono, ‐bis‐ and trispeptides XII [4c], and N‐phosphanylalkyl‐ and ‐arylacyl amido acids XIII‐XV ,[3b], [8b], [11d], were prepared by “Phospha‐Mannich”, Schiff‐base or acyl amide condensation or other reactions. The above mentioned 3‐phosphaprolines ( PP and BPP ) and the acyclic α‐phosphanyl amino acids imply a P‐C‐N structure motif and syntheses via two‐ or three‐component reactions could be possible, like for phosphanylmethyl amino acids.…”

Section: Early Results and Consideration Of Convenient Routes To α‐Phmentioning

confidence: 99%

“…α‐Phosphanyl amino acids were almost unknown before our investigations but seemed us worth studying because of the close distance of the phosphanyl group to the asymmetric carbon‐atom. Also, the stability of various acyclic and heterocyclic P‐CH 2 ‐N‐CHR‐COOH compounds with the proton close at the usually acid‐sensitive N,P‐acetal substructure can provide intriguing characteristics. The currently known types of α‐phosphanyl amino acids, i.e.…”

Section: Introductionmentioning

confidence: 99%

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Chemistry of α‐Phosphanyl α‐Amino Acids

2018

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After a short introduction on potential applications and types of phosphanyl-substituted α-amino acids the current knowledge on syntheses of acyclic and heterocyclic α-phosphanyl α-amino acids, their structural features, properties, reac-[a] and coordination compounds. Dmitry Yakhvarov is a specialist in phosphorus, physical, inorganic, coordination and organoelement chemistry, catalysis and electrochemistry. His main research interests are focused on the development of new technologies for the preparation of organophosphorus and organoelement compounds, including organometallics, by electrochemical methods based on the principles of "green chemistry". In 2016 he was awarded the honorary title of "Professor of the Russian Academy of Sciences". Joachim Heinicke studied chemistry at the Martin-Luther-University Halle and performed his PhD work under supervision of Prof. A. Tzschach. Continuing work in his group, he started besides contract research on high-purity doting compounds for electronic materials investigations on various amino-and hydroxy-functional As and P compounds, including heterocycles with dicoordinated As and P, stabilized by π-bonds. After habilitation this research was extended to silylenes and later also to germylenes and carbenes. Complex chemical and catalytic studies with o-hydroxyarylphosphanes were started after moving to the University Greifswald (1990 Docent, 1992 Professor), for some years in cooperation with Prof. Keim (Aachen). The change of the education focus to biochemistry led then to investigations on the α-phosphanyl amino acids, stimulated also by some early experiments in this direction. After retirement in 2012 he is still active to round off unpublished work. Eur. J. Inorg. Chem. 2019, 1507-1518

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Section: Early Results and Consideration Of Convenient Routes To α‐Phmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemistry of α‐Phosphanyl α‐Amino Acids

2018

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“…Disubstitution at the primary amino group, typical for many phosphanylmethylations, was never observed. The mono-phosphanylmethylations, known also for Nprimary a-amino acids such as alanine under mild conditions, 19 may thus be attributed to the presence of the COOH group in a-position.…”

Section: Synthesismentioning

confidence: 99%

α-Phosphanyl amino acids: synthesis, structure and properties of alkyl and heterocyclic N-substituted diphenylphosphanylglycines

et al. 2015

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“…P,NH-acetals, obtained by reactions of secondary phosphines with a-amino acids and CH 2 O. [138,225] Me 78 [1] -* Et Me 87 [1] -* Me 93 [1] -* Et Et 77, [2] 85 [3] -* 72 [4] -34.7 (CDCl 3 ) 30 [5] -29.4** (CD 2 Cl 2 ) i-Pr i-Pr 92 [5] -42.6** (CD 2 Cl 2 ) Et Et 72 [6] -* Et Et 80 [6] -* 10 Et Et 76 [6] -* 11 Et Et 78 [6] -* 12 Et Et (-)* [7,8] -48.3 (CDCl 3 ) 13 70 [9] -37.8 (CDCl 3 )…”

Section: Contentmentioning

confidence: 99%

“…P,NH-acetals, obtained by reactions of secondary phosphines with a-amino acids and CH2O. [138,225] Entry R R' R" Yield, % [226,227] 3 i-Pr Et 2 O 85 [226,227] 4 t-Bu Et 2 O 83, [226,227] 92 [228] 5 t-Bu MeOH 54 [190] 6…”

Section: Entrymentioning

confidence: 99%