KHSO4-mediated synthesis of α-amino phosphonates under a neat condition and their 31P NMR chemical shift assignments

Tetrahedron Letters

Volumn 51, Issue 43, 2010, Pages 5708-5712

  Thirumurugan, P ^a   Nandakumar, A ^a   Priya, N Sudha ^a   Muralidaran, D ^a   Perumal, P T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO PHOSPHONIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; POTASSIUM DERIVATIVE; POTASSIUM HYDROGEN SULFATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 77957114917     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.066     Document Type: Article

References (24)

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21. General procedure for the synthesis of α-amino phosphonate derivatives: A mixture of aldehyde (1 mmol), substituted aromatic or aliphatic amine (1 mmol), diethyl phosphate (1.5 mmol), and potassium hydrogen sulfate (20 mol %) under a neat condition was stirred at room temperature. After completion of the reaction as indicated by TLC, it was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The crude product was chromatographed and the appropriate isolated yield is shown in Tables 2 and 3.
22. 3P: C, 54.45; H, 5.22; N, 3.02. Found: C, 54.37; H, 5.24; N, 3.01.
23. 3P: C, 62.97; H, 5.49; N, 8.47. Found: C, 62.73; H, 5.45; N, 8.50.
24. Crystallographic data of compound 4f in this Letter have been deposited with the Cambridge Crystallographic Data centre as supplemental publication no. CCDC 775941. Copies of the data can be obtained, free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 01223 336033 or email: deposit@ccdc.cam.ac.uk ).