One-pot synthesis of α-amino acids from CO2 using a bismetal reagent with Si-B bond

Organic Letters

Volumn 14, Issue 24, 2012, Pages 6202-6205

  Mita, Tsuyoshi ^a   Chen, Jianyang ^a   Sugawara, Masumi ^a   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBON DIOXIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GLYCINE; IMINE; LEUCINE; SERINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CARBON DIOXIDE; GLYCINE; IMINES; INDICATORS AND REAGENTS; LEUCINE; MOLECULAR STRUCTURE; SERINE; STEREOISOMERISM;

EID: 84871574393     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302952r     Document Type: Article

References (52)

1. Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889
2. Duthaler, R. O. Tetrahedron 1994, 50, 1539
3. Kreuzfeld, H. J.; Döbler, C.; Schmidt, U.; Krause, H. W. Amino Acids 1996, 11, 269
4. Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517
5. Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013
6. Ma, J.-A. Angew. Chem., Int. Ed. 2003, 42, 4290
7. Beak, P.; Johnson, T. A.; Kim, D. D.; Lim, S. H. Top. Organomet. Chem. 2003, 5, 139
8. Nájera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584
9. Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747
10. Sakakura, T.; Choi, J.-C.; Yasuda, H. Chem. Rev. 2007, 107, 2365
11. Mori, M. Eur. J. Org. Chem. 2007, 4981
12. Correa, A.; Martín, R. Angew. Chem., Int. Ed. 2009, 48, 6201
13. Riduan, S. N.; Zhang, Y. Dalton Trans. 2010, 39, 3347
14. Boogaerts, I. I. F.; Nolan, S. P. Chem. Commun. 2011, 47, 3021
15. Ackermann, L. Angew. Chem., Int. Ed. 2011, 50, 3842
16. Zhang, Y.; Riduan, S. N. Angew. Chem., Int. Ed. 2011, 50, 6210
17. Cokoja, M.; Bruckmeier, C.; Rieger, B.; Herrmann, W. A.; Kühn, F. E. Angew. Chem., Int. Ed. 2011, 50, 8510
18. Mita, T.; Chen, J.; Sugawara, M.; Sato, Y. Angew. Chem., Int. Ed. 2011, 50, 1393
19. Mita, T.; Higuchi, Y.; Sato, Y. Chem.-Eur. J., doi: 10.1002/chem. 201202332
20. Mita, T.; Sugawara, M.; Hasegawa, H.; Sato, Y. J. Org. Chem. 2012, 77, 2159
21. 2Si-Bpin, see: Suginome, M.; Matsuda, T.; Ito, Y. Organometallics 2000, 19, 4647
22. For a review on bismetal reagents, see: Beletskaya, I.; Moberg, C. Chem. Rev. 2006, 106, 2320
23. Levin., V. V.; Dilman, A. D.; Belyakov, P. A.; Struchkova, M. I.; Tartakovsky, V. A. Eur. J. Org. Chem. 2008, 5226
24. Gritsenko., R. T.; Levin, V. V.; Dilman, A. D.; Belyakov, P. A.; Struchkova, M. I.; Tartakovsky, V. A. Tetrahedron Lett. 2009, 50, 2994
25. Kosobokov, M. D.; Dilman, A. D.; Struchkova, M. I.; Belyakov, P. A.; Hu, J. J. Org. Chem. 2012, 77, 2080
26. Ballweg, D. M.; Miller, R. C.; Gray, D. L.; Scheidt, K. A. Org. Lett. 2005, 7, 1403
27. Vyas, D. J.; Fröhlich, R.; Oestreich, M. Org. Lett. 2011, 13, 2094
28. Ohno, M.; Tanaka, H.; Komatsu, M.; Ohshiro, Y. Synlett 1991, 919
29. Singh, R. P.; Shreeve, J. M. Chem. Commun. 2002, 1818
30. Babadzhanova, L. A.; Kirij, N. V.; Yagupolskii, Y. L. J. Fluorine Chem. 2004, 125, 1095
31. Petko, K. I.; Kot, S. Y.; Yagupolskii, L. M. J. Fluorine Chem. 2008, 129, 301
32. Effenberger, F.; Spiegler, W. Chem. Ber. 1985, 118, 3900
33. Mita, T.; Michigami, K.; Sato, Y. Org. Lett. 2012, 14, 3462
34. For the stabilization of lithium carbanion by a Boc group, see: Park, Y. S.; Beak, P. J. Org. Chem. 1997, 62, 1574
35. Emsley, J. The Elements, 3 rd ed.; Oxford University Press: New York, 1998.
36. Walter, C.; Auer, G.; Oestreich, M. Angew. Chem., Int. Ed. 2006, 45, 5675
37. Walter, C.; Oestreich, M. Angew. Chem., Int. Ed. 2008, 47, 3818
38. Walter, C.; Fröhlich, R.; Oestreich, M. Tetrahedron 2009, 65, 5513
39. Vyas, D. J.; Oestreich, M. Angew. Chem., Int. Ed. 2010, 49, 8513
40. Lee, K.-S.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 2898
41. Welle, A.; Petrignet, J.; Tinant, B.; Wouters, J.; Riant, O. Chem.-Eur. J. 2010, 16, 10980
42. Ibrahem, I.; Santoro, S.; Himo, F.; Córdova, A. Adv. Synth. Catal. 2011, 353, 245
43. Kleeberg, C.; Feldmann, E.; Hartmann, E.; Vyas, D. J.; Oestreich, M. Chem.-Eur. J. 2011, 17, 13538
44. Calderone, J. A.; Santos, W. L. Org. Lett. 2012, 14, 2090
45. O'Brien, J. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2011, 133, 7712
46. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912
47. Hiyama, T.; Obayashi, M. Tetrahedron Lett. 1983, 24, 4109
48. Hiyama, T.; Obayashi, M.; Sawahata, M. Tetrahedron Lett. 1983, 24, 4113
49. For borylation of imines using pinB-Bpin by a methoxide anion without transition metal catalysts, see: Solé, C.; Gulyás, H.; Fernández, E. Chem. Commun. 2012, 48, 3769
50. It is also possible that the boron atom is prone to be activated by a fluoride through the coordination of pinacol oxygen to a protic additive. See: Awano, T.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2011, 133, 20738
51. Lipkowski, A. W. Pol. J. Chem. 1981, 55, 1725
52. Juaristi, E.; Escalante, J.; Lén-Romo, J. L.; Reyes, A. Tetrahedron: Asymmerty 1998, 9, 715