(S,S)-(+)-pseudoephedrine α-iminoglyoxylamide as a chiral glycine cation equivalent: A modular and flexible approach to enantioenriched α-amino ketones

Organic Letters

Volumn 10, Issue 12, 2008, Pages 2613-2616

  Ruiz, Nerea ^a   Vicario, Jose L ^a   Badía, Dolores ^a   Carrillo, Luisa ^a   Alonso, Beatriz ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCINE; KETONE; LITHIUM; ORGANOMETALLIC COMPOUND; PSEUDOEPHEDRINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; GLYCINE; KETONES; LITHIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PSEUDOEPHEDRINE; STEREOISOMERISM;

EID: 48849095174     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800934r     Document Type: Article

References (52)

1. For some reviews see: (a) Meester, W. J. N.; van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2003, 2519.
2. (b) Taggi, A. E.; Hafez, A. M.; Letcka, T. Acc. Chem. Res. 2003, 36, 10.
3. For some reviews on the asymmetric synthesis of α-amino acids, see: (a) Najera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584.
4. (b) Groger, H. Chem. Rev. 2003, 103, 2795.
5. For some recent examples, see: (a) Aydin, J.; Kumar, K. S.; Sayah, M. J.; Wallner, O. A.; Szabo, K. J. J. Org. Chem. 2007, 72, 4689.
6. (b) Colombo, F.; Annunziata, R.; Benaglia, M. Tetrahedron Lett. 2007, 48, 2687.
7. (c) Fuchibe, K.; Hatemata, R.; Akiyama, R. Tetrahedron 2006, 62, 11304.
8. (d) Kiyohara, H.; Nakamura, Y.; Matsubara, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 1615.
9. (e) Basra, S.; Fennie, M. W.; Kozlowski, M. C. Org. Lett. 2006, 8, 2659.
10. (f) Kong, J.-R.; Cho, C.-W.; Krische, M. J. J. Am. Chem. Soc. 2005, 127, 11269.
11. (g) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42.
12. (h) Hamada, T.; Manabe, K.; Kobayashi, S. Angew. Chem., Int. Ed. 2003, 42, 3927.
13. (i) Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1999, 64, 4844.
14. (j) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997.
15. For some selected recent examples, see: (a) Kulkarni, N. A.; Yao, C.-F.; Chen, K. Tetrahedron 2007, 63, 7816.
16. (b) Beenen, M. A.; Weix, D. J.; Ellman, J. A. J. Am. Chem. Soc. 2006, 128, 6304.
17. (c) Viso, A.; Fernandez de la Pradilla, R.; Flores, A.; Garcia, A.; Tortosa, M.; Lopez-Rodriguez, M. L. J. Org. Chem. 2006, 71, 1442.
18. (d) Neelesh, A. K. Chen, K. Tetrahedron Lett. 2006, 47, 611.
19. (e) Berree, F.; Debache, A.; Marsac, Y.; Collet, B.; Bleiz, P. G.; Carboni, B. Tetrahedron 2006, 62, 4027.
20. (f) Ueda, M.; Miyabe, H.; Sugino, H.; Naito, T. Org. Biomol. Chem. 2005, 3, 1124.
21. (g) Singh, N.; Anand, R. D.; Trehan, S. Tetrahedron Lett. 2004, 45, 2911.
22. (h) Bull, S. D.; Davies, S. G.; Garner, A. C.; Savory, E. D.; Snow, E. J.; Smith, A. D. Tetrahedron: Asymmetry 2004, 15, 3989.
23. (i) Wipf, P.; Stephenson, C. R. J. Org. Lett. 2003, 5, 2449.
24. (j) Chiev, K. P.; Roland, S.; Mangeney, P. Tetrahedron: Asymmetry 2002, 13, 2205.
25. (k) Di Fabio, R.; Alvaro, G.; Bertani, B.; Donati, D.; Giacobbe, S.; Marchioro, C.; Palma, C.; Lynn, S. M. J. Org. Chem. 2002, 67, 7319.
26. (l) Bertrand, M. P.; Coantic, S.; Feray, L.; Nouguier, R.; Perfetti, P. Tetrahedron 2000, 56, 3951.
27. (m) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396.
28. Fiaud, J.-C.; Kagan, H. B. Tetrahedron Lett. 1971, 12, 1019.
29. For the first use of pseudoephedrine as chiral auxiliary, see: (a) Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361.
30. (b) Myers, A. G.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496.
31. For a review, see: (c) Myers, A. G.; Charest, M. G. Handbook of Reagents for Organic Synthesis: Chiral Reagents for Asymmetric Synthesis; Paquette, L. A., Ed.; Wiley Interscience: New York, 2003; p 485.
32. For other examples, see: (d) Iza, A.; Vicario, J. L.; Badia, D.; Carrillo, L. Synthesis 2006, 4065.
33. (e) Vicario, J. L.; Rodriguez, M.; Badia, D.; Carrillo, L.; Reyes, E. Org. Lett. 2004, 6, 3171.
34. (f) Smitrovich, J. H.; Boice, G. N.; Qu, C.; Dimichelle, L.; Nelson, T. D.; Huffman, M. A.; Murry, J.; McNamara, J.; Reider, P. J. Org. Lett. 2002, 4, 1.
35. (g) Hutchison, P. C.; Heightman, T. D.; Procter, D. J. Org. Lett. 2002, 4, 4583.
36. (h) Vicario, J. L.; Badía, D.; Carrillo, L. J. Org. Chem. 2001, 66, 5801.
37. (i) Vicario, J. L.; Badía, D.; Carrillo, L. J. Org. Chem. 2001, 66, 9030.
38. (j) Anakabe, E.; Vicario, J. L; Badía, D.; Carrillo, L.; Yoldi, V. Eur. J. Org. Chem. 2001, 4343.
39. (k) Myers, A. G.; Barbay, J. K.; Zhong, B. J. Am. Chem. Soc. 2001, 123, 7207.
40. (l) Vicario, J. L.; Badía, D.; Domínguez, E.; Rodríguez, M.; Carrillo, L. J. Org. Chem. 2000, 65, 3754.
41. (m) Myers, A. G.; McKinstry, L. J. Org. Chem. 1996, 61, 2428.
42. (a) Reyes, E.; Vicario, J. L.; Carrillo, L.; Badia, D.; Uria, U.; Iza, A. J. Org. Chem. 2006, 71, 7763.
43. (b) Etxebarria, J.; Vicario, J. L.; Badia, D.; Carrillo, L.; Ruiz, N. J. Org. Chem. 2005, 70, 8790.
44. For a detailed study see ref 6a. For other related examples, see: (a) Zhou, X.-T.; Lu, L.; Furkert, D. P.; Wells, C. E.; Carter, R. G. Angew. Chem., Int. Ed. 2006, 45, 7622.
45. (b) Robertson, J.; Dallimore, J. W. P.; Meo, P. Org. Lett. 2004, 6, 3857.
46. (c) White, J. D.; Xu, Q.; Lee, C.-S.; Valeriote, F. A. Org. Biomol. Chem. 2004, 2, 2092.
47. (d) Vicario, J. L.; Badía, D.; Carrillo, L. Tetrahedron: Asymmetry 2003, 14, 489.
48. (e) Vicario, J. L.; Badía, D.; Carrillo, L. Tetrahedron: Asymmetry 2002, 13, 745.
49. (f) Smith, A. B., III; Adams, C. M.; Kozmin, S. A.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 5925. See also refs 6d and 6k.
50. Myers has reported the 1,2-addition of Grignard reagents to N-Boc α-amino amides derived from pseudoephedrine. Myers, A. G.; Yoon, T. Tetrahedron Lett. 1995, 36, 9429.
51. Del Valle, J. R.; Goodman, M. J. Org. Chem. 2004, 69, 8946.
52. We also tested the addition of Grignard reagents to N-benzylglycinamide 3a as reported by Myers for N-Boc- glycinamides (see ref 9), but the reaction proceeded sluggisly and we could not observe the formation of any α-amino ketone product.