One-pot synthesis of α-amino phosphonates from α-amino acids and β-amino alcohols

Tetrahedron Letters

Volumn 46, Issue 45, 2005, Pages 7807-7811

  Boto, Alicia ^a   Gallardo, Juan Antonio ^a   Hernández, Rosendo ^a   Saavedra, Carlos Javier ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

Amino acids; Amino phosphonates; Decarboxylation; Fragmentation; Hypervalent iodine reagents; Radicals

Indexed keywords

ALCOHOL DERIVATIVE; AMINO ACID DERIVATIVE; BETA AMINO ACID; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DECARBOXYLATION; DRUG SYNTHESIS; FRAGMENTATION REACTION; PHOSPHORYLATION;

EID: 26444523953     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.019     Document Type: Article

References (51)

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32. 3 at 70°C unless otherwise stated.
33. 4P 283.0973, found 283.0968.
34. -1. For a discussion on the subject, see: J. Fossey, D. Lefort, and J. Sorba Free Radicals in Organic Chemistry 1995 Wiley Chichester pp 96, 148-149, 223-225 and 295
35. 7P 434.1243, found 434.1248.
36. For very similar compounds, see: C. Yuan, G. Wang, and S. Chen Synthesis 1990 522 524
37. T. Shono, Y. Matsumura, and K. Tsubata Tetrahedron Lett. 22 1981 3249 3252
38. 5P 251.0923, found 251.0935.
39. For a similar result, see: A. Boto, R. Hernández, and E. Suárez Tetrahedron Lett. 40 1999 5945 5948
40. 5P 265.1079, found 265.1089.
41. 6P 280.0950, found 280.0947.
42. H,P = 10.3 Hz), 3.60 (1H, m), 2.61 (1H, m), 2.23 (1H, m), 2.09 (3H, m), 2.01 (3H, s).
43. H 2.46) and 4-H or 2-H was very weak, as expected for 2-H,3α-H trans and 4-H,3α-H trans relationships.
44. H 4.73) was also observed.
45. The nucleophile was added from the apparently more hindered face. For similar results, see: H. Yoda, T. Egawa, and K. Takabe Tetrahedron Lett. 44 2003 1643 1646 and references cited therein
46. 12P 456.1271, found 456.1286.
47. H,P = 11.9 Hz, OMe), 2.14 (3H, s, Ac), 2.12 (3H, s, Ac), 2.05 (3H, s, Ac), 1.99 (3H, s, Ac).
48. The stereochemistry of compounds 27 and 28 was tentatively assigned by comparing the theoretical coupling constants calculated over the minimized structures for both diastereomers and the experimental coupling constants at -50°C. Since at this temperature the interconversion between conformers is very slow, signals for each conformer are recorded in the NMR experiment; the intensity of the signals is related to the conformer population. In our case, the signals of the minor conformations were hardly observed. Presuming that the minimum-energy conformation was the major one, the experimental J would match the theoretical ones.
49. The theoretical J were calculated by using the Karplus-Altona equation implemented in the Macromodel 7.0 program. See: C.A.G. Haasnoot, F.A.A.M. de Leeuw, and C. Altona Tetrahedron 36 1980 2783 2792
50. 3,4 = 4.4 Hz.
51. A. Boto, R. Hernández, and E. Suárez Tetrahedron Lett. 42 2001 9167 9170