Synthesis and application of a chiral diborate

Journal of Organic Chemistry

Volumn 76, Issue 7, 2011, Pages 2324-2327

  Loewer, Yvonne ^a   Weiss, Christine ^a   Biju, Akkattu T ^a   Fröhlich, Roland ^a   Glorius, Frank ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL SHIFT; COUNTERIONS; DIANIONS; NMR ANALYSIS;

BORIC ACID; COUNTERION; DIAMINE; METHYLTRIPHENYLPHOSPHONIUM;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY;

EID: 79953193055     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102559s     Document Type: Article

References (40)

1. Lacour, J.; Linder, D. Science 2007, 317, 462
2. For an excellent overview, see: Adair, G.; Mukherjee, S.; List, B. Aldrichim. Acta 2008, 41, 2
3. For an example for enantioselective reductive amination, see: Hoffmann, S.; Nicoletti, M.; List, B. J. Am. Chem. Soc. 2006, 128, 13074 For related works on counterion directed catalysis, see: Liao, S.; List, B. Angew. Chem., Int. Ed. 2010, 49, 628
4. Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336
5. Martin, N. J. A.; List, B. J. Am. Chem. Soc. 2006, 128, 13368
6. Mayer, S.; List, B. Angew. Chem., Int. Ed. 2006, 45, 4193
7. For one recent example in transfer hydrogenations, see: Rueping, M.; Antonchick, A. P. Angew. Chem., Int. Ed. 2007, 46, 4562 For some other recent examples, see: Rueping, M.; Ieawsuwan, W.; Antonchick, A. P.; Nachtsheim, B. J. Angew. Chem., Int. Ed. 2007, 46, 2097
8. Rueping, M.; Nachtsheim, B. J.; Moreth, S. A.; Bolte, M. Angew. Chem., Int. Ed. 2008, 47, 593
9. Rueping, M.; Antonchick, A. P. Org. Lett. 2008, 10, 1731
10. Rueping, M.; Antonchick, A. P. Angew. Chem., Int. Ed. 2008, 47, 5836
11. Lalonde, R. L.; Wang, J. Z.; Mba, M.; Lackner, A. D.; Toste, F. D. Angew. Chem., Int. Ed. 2010, 49, 598
12. Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496
13. Lacour, J.; Ginglinger, C.; Grivet, C.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 608
14. Ginglinger, C.; Jeannerat, D.; Lacour, J.; Jugé, S.; Uziel, J. Tetrahedron Lett. 1998, 39, 7495
15. Lacour, J.; Ginglinger, C.; Favarger, F.; Torche-Haldimann, S. Chem. Commun. 1997, 2285
16. Frantz, R.; Pinto, A.; Constant, S.; Bernardinelli, G.; Lacour, J. Angew. Chem., Int. Ed. 2005, 44, 5060
17. Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldimann, S. Angew. Chem., Int. Ed. 1998, 37, 2379
18. For a review on shift reagents, see: Wenzel, T. J.; Wilcox, J. D. Chirality 2003, 15, 256
19. Carter, C.; Fletcher, S.; Nelson, A. Tetrahedron: Asymmetry 2003, 14, 1995
20. Llwellyn, D. B.; Adamson, D.; Arndtsen, B. A. Org. Lett. 2000, 2, 4165 For very recent catalytic asymmetric aziridination using borate-based Brønsted acids, see: Desai, A. A.; Wulff, W. D. J. Am. Chem. Soc. 2010, 132, 13100
21. Vetticatt, M. J.; Desai, A. A.; Wulff, W. D. J. Am. Chem. Soc. 2010, 132, 13104
22. Chen, D.; Sundararaju, B.; Krause, R.; Klankermayer, J.; Dixneuf, P. H.; Leitner, W. ChemCatChem 2010, 55
23. Danjo, H.; Hirata, K.; Yoshigai, S.; Azumaya, I.; Yamaguchi, K. J. Am. Chem. Soc. 2009, 131, 1638
24. Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561
25. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520
26. Ishihara, K.; Kuriharu, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920-6930
27. For a useful review on chiral anions, see: Lacour, J.; Hebbe-Viton, V. Chem. Soc. Rev. 2003, 32, 373
28. Tu, T.; Maris, T.; Wuest, J. D. Cryst. Growth Des. 2008, 8, 1541 For some other applications of chiral borates or boronates, see: Reyes, H.; Rivera, J. M.; Farfan, N.; Santillan, R.; Lacroix, P. G.; Lepetit, C.; Nakatani, K. J. Organomet. Chem. 2005, 690, 3737
29. Yu, S.; Lindeman, S.; Tran, C. D. J. Org. Chem. 2008, 73, 2576
30. Cram, D. J.; Helgeson, R. C.; Peacock, S. C.; Kaplan, L. J.; Domeier, L. A.; Domeier, L. A.; Moreau, P.; Koga, K.; Mayer, J. M.; Chao, Y.; Siehel, M. G.; Hoffman, D. H.; Sogah, G. D. Y. J. Org. Chem. 1978, 43, 1930
31. See the Supporting Information for details.
32. Periasamy, M.; Venkatraman, L.; Sivaumar, S.; Kumar, N. S.; Ramanathan, C. R. J. Org. Chem. 1999, 64, 7643 For separation of amino alcohols, see: Periasamy, M.; Kumar, N. S.; Sivakumar, S.; Ran, V. D.; Ramanathan, C. R.; Venkatraman, L. J. Org. Chem. 2001, 66, 3828
33. For some examples, see: Kouklovsky, C.; Langlois, Y. (1 S,2 S)-1,2-Diaminocyclohexane. In Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: New York, 2003.
34. For a comprehensive review, see: Trost, B. M.; Fandrick, D. R. Aldrichim. Acta 2007, 40, 59
35. Kim, H.; Nguyen, Y.; Yen, C. P.-H.; Chagal, L.; Lough, A. J.; Kim, B. M.; Chin, J. J. Am. Chem. Soc. 2008, 130, 12184
36. Perrin, C. L. Org. Magn. Reson. 2005, 16, 11
37. Llewellyn, D. B.; Arndtsen, B. A. Can. J. Chem. 2003, 81, 1280
38. Doering, W. v. E.; Benkhoff, J.; Carleton, P. S.; Pagnotta, M. J. Am. Chem. Soc. 1997, 119, 10947-10955
39. Ratni, H.; Jodry, J. J.; Lacour, J.; Kündig, E. P. Organometallics 2000, 19, 3997
40. Carr, J. M.; Duggan, P. J.; Humphrey, D. G.; Tyndall, E. M. Aust. J. Chem. 2005, 58, 21