Interesting by-products in the synthesis of chiral α- aminophosphinates from enantiopure sulfinimines

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 1991-1994

  Szabó, Andrea ^a   Jászay, Zsuzsa M ^b   Töke, László ^a   Petneházy, Imre ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

Author keywords

Ethyl phenylphosphonic acid; Side reaction of p tolylsulfinimines; Aminophosphinic acids

Indexed keywords

IMINE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION;

EID: 1242293797     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.151     Document Type: Article

References (20)

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13. 3), 7.33-7.67 (m, 4H, ArH), 7.71-7.87 (m, 4H, ArH), 9.08 (s, 1H, CH=N).
14. + (calcd 292.3).
15. To give a chemical proof for the structure of 9 , 6 was oxidized by m-chloroperbenzoic acid. The product was monitored by FAB-MS, the fragmentation was identical with that of 9.
16. 3) δ=38.7 , 38.5 ppm.
17. 3) δ=40.3 , 39.4, 38.8, 38.5.
18. 6-DMSO) δ: 34.69.
19. The (R)-enantiomer of ethyl α-benzylamino-phenylphosphinic acid is known from the literature, and has been isolated by resolution and by repeated crystallization from the diastereomeric mixture of its ester. The absolute configuration was then determined by X-ray crystallography. See: Belov Yu.P., Rakhnovich G.B., Davankov V.A., Godovikov N.N., Aleksandrov G.G., Struchkov Yu.T. Izv. Akad. Nauk. 5:1980;1125.
20. 2,2,6,6-Tetramethylpiperidine-1-oxyl (0.1 equiv), 1 equiv of imine 5a or 5e and 2 equiv of ethyl phenylphosphinate 1 were kept at 70°C in toluene.