A concise three-component synthesis of α-amino esters derived from phenylglycine and phenylalanine

Tetrahedron Letters

Volumn 49, Issue 50, 2008, Pages 7121-7123

  Haurena, Caroline ^a   Sengmany, Stéphane ^a   Huguen, Paul ^a   Gall, Erwan Le ^a   Martens, Thierry ^a   Troupel, Michel ^a  

^a CNRS Université Paris Est Créteil Val de Marne   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ESTER DERIVATIVE; AROMATIC COMPOUND; BENZILIC ACID; ESTER DERIVATIVE; ETHYL GLYOXYLATE; GLYOXYLIC ACID DERIVATIVE; PHENYLALANINE; PHENYLGLYCINE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 54449083952     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.137     Document Type: Article

References (29)

1. For some selected examples, see:. Sardina J.F., and Rapoport H. Chem. Rev. 96 (1996) 1825-1872
2. Rutjes F.P.J.T., Wolf L.B., and Schoemaker H.E. J. Chem. Soc., Perkin Trans. 1 (2000) 4197-4212
3. Jarvo E.R., and Miller S.J. Tetrahedron 58 (2002) 2481-2495
4. Kaiser J., Kinderman S.S., van Esseveldt B.C.J., van Delft F.L., Schoemaker H.E., Blaauw R.H., and Rutjes F.P.J.T. Org. Biomol. Chem. 3 (2005) 3435-3467
5. Kazmaier U. Angew. Chem., Int. Ed. 44 (2005) 2186-2188
6. Williams R.M. Synthesis of Optically Active Amino Acids (1989), Pergamon Press, Oxford University Press
7. Duthaler R.O. Tetrahedron 50 (1994) 1539-1650
8. Fornicola R.S., Oblinger E., and Montgomery J. J. Org. Chem. 63 (1998) 3528-3529
9. Alcaide B., Almendros P., and Aragoncillo C. Chem. Eur. J. 8 (2002) 3646-3652
10. Park H., Jeong B., Yoo M.S., Lee J., Park M., Lee Y.J., Kim M., and Jew S. Angew. Chem., Int. Ed. 41 (2002) 3036-3038
11. Petasis N.A., and Akritopoulou I. Tetrahedron Lett. 34 (1993) 583-586
12. Petasis N.A., Goodman A., and Zavialov I.A. Tetrahedron 48 (1997) 16463-16470
13. Petasis N.A., and Zavialov A. J. Am. Chem. Soc. 119 (1997) 445-446
14. Petasis N.A., and Zavialov I.A. J. Am. Chem. Soc. 120 (1998) 11798-11799
15. Petasis N.A., and Boral S. Tetrahedron Lett. 42 (2001) 539-542
16. Prakash G.K.S., Mandal M., Schweizer S., Petasis N.A., and Olah G.A. J. Org. Chem. 67 (2002) 3718-3723
17. Nanda K.K., and Trotter B.W. Tetrahedron Lett. 46 (2005) 2025-2028
18. Grigg R., Sridharan V., and Thayaparan A. Tetrahedron Lett. 44 (2003) 9017-9019
19. Katritzky described the displacement of preformed benzotriazole-derived iminium equivalents by organometallics for the synthesis of phenylglycine and phenylalanine derivatives, see:. Katritzky A.R., Urogdi L., and Mayence A. Synthesis (1989) 323-327
20. Le Gall E., Troupel M., and Nédélec J.-Y. Tetrahedron Lett. 47 (2006) 2497-2500
21. Le Gall E., Troupel M., and Nedelec J.-Y. Tetrahedron 62 (2006) 9953-9965
22. Sengmany S., Le Gall E., Le Jean C., Troupel M., and Nédélec J.-Y. Tetrahedron 63 (2007) 3672-3681
23. Sengmany S., Le Gall E., and Troupel M. Synlett (2008) 1031-1035
24. Organozinc reagents are known to be alkaline compounds.
25. Fillon H., Gosmini C., and Périchon J. J. Am. Chem. Soc. 125 (2003) 3867-3870
26. General procedure starting from aryl bromides: A dried 100 mL round-bottomed flask was flushed with argon and charged with acetonitrile (40 mL). Cobalt bromide (0.66 g, 3 mmol), zinc bromide (0.68 g, 3 mmol), phenyl bromide (0.32 mL, 3 mmol), zinc dust (6 g, 92 mmol) and trifluoromethanesulfonic acid (0.2 mL) were added to the solution under vigorous stirring (ca. ∼500 rpm). After ca. 15 min, the aryl bromide (30 mmol) was added to the solution and as soon as the exothermic reaction had began (ca. 5 min), a water bath at room temperature was used to moderate the temperature of the medium. After 30 min, stirring was stopped and the surrounding solution was taken up using a syringe and transferred into another flask containing the amine (10 mmol) and ethyl glyoxylate (∼50% solution in toluene, 2.6 mL, ∼13 mmol) in 10 mL acetonitrile. After 5 min at room temperature, the mixture was heated at 50 °C for 3-4 h using an oil bath. The reaction was then quenched with a saturated ammonium chloride solution (150 mL) and the organic products extracted with dichloromethane (2 × 100 mL). After removal of the solvent, a chromatographic purification on neutral alumina using a pentane/dichloromethane mixture as an eluant (80/20→10/90) afforded the pure product.
27. General procedure starting from benzyl bromides: A dried 100 mL round-bottomed flask was flushed with argon and charged with acetonitrile (40 mL). Zinc dust (2 g, 30 mmol) and trifluoromethanesulfonic acid (0.2 mL) were added under vigorous stirring (ca. ∼500 rpm). After 5 min, the amine (10 mmol), ethyl glyoxylate (∼50% solution in toluene, 2.6 mL, ∼13 mmol) and the functionalized benzyl bromide (22 mmol) were added to the solution and allowed to react for 1 h at room temperature. The reaction was quenched with a saturated ammonium chloride solution (150 mL) and the organic products extracted with dichloromethane (2 × 100 mL). After removal of the solvent, a chromatographic purification on neutral alumina using a pentane/dichloromethane mixture as an eluant (80/20→10/90) afforded the pure product. Alternatively, the pure α-amino ester could be obtained from the crude oil using an acid-base work-up, as detailled in Ref. 7b.
28. De Lamo Marin S., Martens T., Mioskowski C., and Royer J. J. Org. Chem. 70 (2005) 10592-10595
29. Verkade J.M.M., van Hemert L.J.C., Quaedflieg P.J.L.M., Alsters P.L., van Delft F.L., and Rutjes F.P.J.T. Tetrahedron Lett. 47 (2006) 8109-8113