Synthesis and Structure of Planar Chiral, Bifunctional Aminoboronic Acid Ferrocene Derivatives

Organometallics

Volumn 26, Issue 9, 2007, Pages 2414-2419

  Batsanov, Andrei S ^a   Hérault, Damien ^a   Howard, Judith A K ^a   Patrick, Leonard G F ^a   Probert, Michael R ^a   Whiting, Andrew ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; INORGANIC ACIDS; REDUCTION; SYNTHESIS (CHEMICAL);

BORONIC ACID; BROMINATION; ENANTIOMERIC EXCESS; FERROCENE; METALATION;

AMIDES;

EID: 34248524652     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om070038l     Document Type: Article

References (37)

1. (a) Zhu, L.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 3676-3677.
2. (b) Zhu, L.; Zhong, Z.; Anslyn, E. V. J. Am. Chem. Soc. 2005, 127, 4260-4269.
3. (a) Norrild, J. C.; Søtofte, I. J. Chem. Soc., Perkin Trans. 2002, 2, 303-311.
4. (b) Orl, A.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1995, 1771-1772.
5. (a) Ward, C. J.; Patel, P.; James, T. D. J. Chem. Soc., Perkin Trans. 2002, 1, 462-470.
6. (b) Zhao, J.; James, T. D. Chem. Commun. 2005, 1889-1891.
7. Dowlut, M.; Hall, D. G. J. Am. Chem. Soc. 2006, 128, 4226-4227.
8. Nguyen, B. T.; Wiskur, S. L.; Anslyn, E. V. Org. Lett. 2004, 6, 2499-2501.
9. (a) Letsinger, R. L.; Dandegaonker, S. H. J. Am. Chem. Soc. 1959, 81, 498-501.
10. (b) Letsinger, R. L.; MacLean, D. B. J. Am. Chem. Soc. 1963, 85, 2230-2236.
11. (a) Hawkins, R. T.; Snyder, H. R. J. Org. Chem. 1960, 82, 3863-3866.
12. (b) Toyota, S.; Futawaka, T.; Asakura, M.; Ikeda, H.; Oki, M. Organomet. 1998, 17, 4155-4163.
13. (a) Wiskur, S. L.; Lavigne, J. J.; Ait-Haddou, H.; Lynch, V.; Chiu, Y. H.; Canary, J. W.; Anslyn, E. V. Org. Lett. 2001, 3, 1311-1314.
14. (b) Norrild, J. C.; Søtofte, I. J. Chem. Soc., Perkin Trans. 2001, 2, 727-732.
15. (c) Norrild, J. C. J. Chem. Soc., Perkin Trans. 2001, 2, 719-726.
16. (d) Bresner, C.; Aldridge, S.; Fallis, I. A.; Jones, C.; Ooi, L.-L. Angew. Chem., Int. Ed. 2005, 44, 3606-3609.
17. (a) Giles, R. L.; Howard, J. A. K.; Patrick, L. G. F.; Probert, M. R.; Smith, G. E.; Whiting, A. J. Organomet. Chem. 2003, 680, 257-262.
18. (b) Coghlan, S. W.; Giles, R. L.; Howard, J. A. K.; Probert, M. R.; Smith, G. E.; Whiting, A. J. Organomet. Chem. 2005, 690, 4784-4793.
19. (c) Blatch, A. J.; Chetina, O. V.; Howard, J. A. K.; Patrick, L. G. F.; Smethurst, C. A.; Whiting, A. Org. Biomol. Chem. 2006, 4, 3297-3302.
20. Arnold, K.; Davies, B.; Giles, R. L.; Grosjean, C.; Smith, G. E.; Whiting, A. Adv. Synth. Catal. 2006, 348, 813-820.
21. (a) Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 685-686.
22. (b) Metallinos, C.; Szillat, H.; Taylor, N. J.; Snieckus, V. Adv. Synth. Catal. 2003, 345, 370-382.
23. (a) Silva, M. E. N. P. R. A.; Pombeiro, A. J. L.; Fraústo da Silva, J. J. R.; Herrman, R.; Deus, N.; Bozak, R. E. J. Organomet. Chem. 1994, 480, 81-90.
24. (b) Marr, G.; Moore, R. E.; Rockett, B. W. Tetrahedron Lett. 1968, 2521-2534.
25. Neto, A. F.; Miller, J.; Faria de Andrade, V.; Fujimoto, S. Y.; Maísa de Freitas, A.; Archanjo, F. C.; Darin, V. A.; Andrade e Silva, M. L.; Borges A. D. L.; Del Ponte, G. Z. Anorg. Allg. Chem. 2002, 628, 209-216.
26. Pickett, T. E.; Roca, F. X.; Richards, C. J. J. Org. Chem. 2003, 68, 2592-2599.
27. Routaboul, L.; Chiffre, J.; Balavoine, G. G. A.; Daran, J. C.; Manoury, E. J. Organomet. Chem. 2001, 637-659, 364-317.
28. (a) Quach, T. D.; Batey, R. A.; Lough, A. J. Acta Crystallogr. Sect. E 2001, 57, o688-o689.
29. (b) Conole, G.; Clough, A.; Whiting, A. Acta Crystallogr. Sect. C 1995, 51, 1056-1059.
30. (a) Pickett, T. E.; Richards, C. J. Tetrahedron Lett. 1999, 40, 5251-5254.
31. (b) Nesmeyanov, A. N.; Kochetkova, N. S.; Leonova, E. V.; Fedin, E. I.; Petrovskii, P. V. J. Organomet. Chem. 1972, 39, 173-177.
32. (c) Koridze, A. A.; Petrovskii, P. V.; Mokhov, A. I.; Lutsenko, A. I. J. Organomet. Chem. 1977, 136, 57-63.
33. (d) Koridze, A. A.; Petrovskii, P. V.; Gubin, S. P.; Sokolov, V. I.; Mokhov, A. I. J. Organomet. Chem. 1977, 136, 65-71.
34. Sheldrick, G. M. SADABS, version 2.10; Bruker-Nonius AXS: Madison, WI, 2003.
35. Sheldrick, G. M. SHELXTL, version 6.14; Bruker-Nonius AXS: Madison, WI, 2003.
36. (a) Flack, H. D. Acta Crystallogr. Sect. A 1983, 39, 876-881.
37. (b) Flack, H. D.; Bernardinelli, G. J. Appl. Crystallogr. 2000, 33, 1143-1148.