One-step synthesis of racemic α-amino acids from aldehydes, amine components, and gaseous CO2 by the aid of a bismetal reagent

Chemistry - A European Journal

Volumn 19, Issue 3, 2013, Pages 1123-1128

  Mita, Tsuyoshi ^a   Higuchi, Yuki ^a   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

aldehydes; amino acids; C C bond formation; carbon dioxide; umpolung

Indexed keywords

BUILDING BLOCKES; C-C BOND FORMATION; HIGH STABILITY; HIGH YIELD; HUMAN LIVES; ONE POT; ONE STEP SYNTHESIS; ORGANIC SYNTHESIS; PROTON SOURCE; STANNANE; STANNYL ANIONS; UMPOLUNG;

ALDEHYDES; AMINO ACIDS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; PROTONS; SULFUR COMPOUNDS; TIN;

CARBON DIOXIDE;

ALDEHYDE; AMINE; AMINO ACID; CARBON DIOXIDE; CESIUM; CESIUM FLUORIDE; FLUORIDE; ORGANOTIN COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; AMINES; AMINO ACIDS; CARBON DIOXIDE; CESIUM; FLUORIDES; MOLECULAR STRUCTURE; ORGANOTIN COMPOUNDS; STEREOISOMERISM;

EID: 84872175394     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201202332     Document Type: Article

References (47)

1. 1a, W. S. Knowles, Acc. Chem. Res. 1983, 16, 106
2. 1b, R. M. Williams, J. A. Hendrix, Chem. Rev. 1992, 92, 889
3. 1c, R. O. Duthaler, Tetrahedron 1994, 50, 1539
4. 1d, H. J. Kreuzfeld, C. Döbler, U. Schmidt, H. W. Krause, Amino Acids 1996, 11, 269
5. 1e, C. Cativiela, M. D. Díaz- de- Villegas, Tetrahedron: Asymmetry 1998, 9, 3517
6. 1f, K. Maruoka, T. Ooi, Chem. Rev. 2003, 103, 3013
7. 1g, J.- A. Ma, Angew. Chem. 2003, 115, 4426;
8. Angew. Chem. Int. Ed. 2003, 42, 4290
9. 1h, C. Nájera, J. M. Sansano, Chem. Rev. 2007, 107, 4584.
10. 2a, V. A. Soloshonok, X. Tang, V. J. Hruby, Tetrahedron 2001, 57, 6375
11. 2b, T. K. Ellis, C. H. Martin, G. T. Tsai, H. Ukei, V. A. Soloshonok, J. Org. Chem. 2003, 68, 6208.
12. For a recent efficient α- amino acid synthesis, see:, S. J. Zuend, M. P. Coughlin, M. P. Lalonde, E. N. Jacobsen, Nature 2009, 461, 968.
13. 4a, A. Strecker, Justus Liebigs Ann. Chem. 1850, 75, 27; for a review, see
14. 4b, H. Gröger, Chem. Rev. 2003, 103, 2795.
15. For a review, see:, A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300;
16. Angew. Chem. Int. Ed. 2000, 39, 3168.
17. 6, T. Mita, J. Chen, M. Sugawara, Y. Sato, Angew. Chem. 2011, 123, 1429;
18. Angew. Chem. Int. Ed. 2011, 50, 1393.
19. 7a, J. B. F. N. Engberts, J. Strating, Recl. Trav. Chim. Pays- Bas 1965, 84, 942
20. 7b, A. M. Kanazawa, J.- N. Denis, A. E. Greene, J. Org. Chem. 1994, 59, 1238
21. 7c, T. Mecozzi, M. Petrini, J. Org. Chem. 1999, 64, 8970
22. 7d, A. G. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 12964.
23. 8a, T. Sakakura, J.- C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365
24. 8b, M. Mori, Eur. J. Org. Chem. 2007, 4981
25. 8c, A. Correa, R. Martín, Angew. Chem. 2009, 121, 6317;
26. Angew. Chem. Int. Ed. 2009, 48, 6201
27. 8d, S. N. Riduan, Y. Zhang, Dalton Trans. 2010, 39, 3347
28. 8e, I. I. F. Boogaerts, S. P. Nolan, Chem. Commun. 2011, 47, 3021
29. 8f, L. Ackermann, Angew. Chem. 2011, 123, 3926;
30. Angew. Chem. Int. Ed. 2011, 50, 3842
31. 8g, Y. Zhang, S. N. Riduan, Angew. Chem. 2011, 123, 6334;
32. Angew. Chem. Int. Ed. 2011, 50, 6210
33. 8h, M. Cokoja, C. Bruckmeier, B. Rieger, W. A. Herrmann, F. E. Kühn, Angew. Chem. 2011, 123, 8662;
34. Angew. Chem. Int. Ed. 2011, 50, 8510.
35. 10a, T. Mita, Y. Higuchi, Y. Sato, Org. Lett. 2011, 13, 2354
36. 10b, T. Mita, Y. Higuchi, Y. Sato, Synthesis 2012, 194.
37. 11a, R. K. Bhatt, J. Ye, J. R. Falck, Tetrahedron Lett. 1994, 35, 4081
38. 11b, J. Busch- Petersen, Y. Bo, E. J. Corey, Tetrahedron Lett. 1999, 40, 2065
39. 11c, R. Blanc, L. Commeiras, J.- L. Parrain, Adv. Synth. Catal. 2010, 352, 661.
40. 12, W. R. McKay, G. R. Proctor, J. Chem. Soc. Perkin Trans. 1 1981, 2435.
41. 13, T. Mita, M. Sugawara, H. Hasegawa, Y. Sato, J. Org. Chem. 2012, 77, 2159.
42. 15a, D. Seebach, D. Enders, Angew. Chem. 1975, 87, 1;
43. Angew. Chem. Int. Ed. Engl. 1975, 14, 15
44. 15b, P. Beak, D. B. Reitz, Chem. Rev. 1978, 78, 275.
45. 16, E. S. Petrov, M. I. Terekhova, R. G. Mirskov, M. G. Voronkov, A. I. Shatenshtein, Dokl. Chem. 1975, 221, 193 (English Translation).
46. 18a, D. Enders, M. Seppelt, T. Beck, Adv. Synth. Catal. 2010, 352, 1413; for the original procedure, see
47. 18b, P. Sun, S. M. Weinreb, J. Org. Chem. 1997, 62, 8604.