Boron-based diastereomerism and enantiomerism in imine complexes - Determination of the absolute configuration at boron by CD spectroscopy

European Journal of Organic Chemistry

Volumn , Issue 31, 2008, Pages 5221-5225

  Braun, Manfred ^a   Schlecht, Sebastian ^a   Engelmann, Marco ^a   Frank, Walter ^a   Grimme, Stefan ^b  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Boron; Chirality; Circular dichroism; Stereochemistry

Indexed keywords

EID: 55049128636     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800787     Document Type: Article

References (29)

1. For reviews, see: M. R. Barbachyn, C. R. Johnson, in Asymmetric Synthesis, vol. 4 (Eds.: J. D. Morrison, J. W. Scott), Academic Press, San Diego, 1984, chapter 2;
2. D. Valentine Jr., in Asymmetric Synthesis, vol. 4 (Eds.: J. D. Morrison, J. W. Scott), Academic Press, San Diego 1984, chapter 3;
3. F. A. Davis, R. H. Jenkins Jr., in Asymmetric Synthesis, vol. 4 (Eds.: J. D. Morrison, J. W. Scott), Academic Press, San Diego 1984, chapter 4;
4. C. A. Maryanoff, B. E. Maryanoff, in Asymmetric Synthesis, vol. 4 (Eds.: J. D. Morrison, J. W. Scott), Academic Press, San Diego, 1984, chapter 5.
5. a) E. Vedejs, R. W. Chapman, S. Lin, M. Müller, D. R. Powell, J. Am. Chem. Soc. 2000, 122, 3047-3052;
6. b) C. S. Shiner, C. M. Garner, R. C. Haltiwanger, J. Am. Chem. Soc. 1985, 107, 7167-7172;
7. c) H. I. Beltrán, L. S. Zamudio-Rivera, T. Mancilla, R. Santillan, N. Farfán, J. Organomet. Chem. 2002, 657, 194-204;
8. d) H. I. Bertrán, S. J. Alas, R. Santillan, N. Farfán, Can. J. Chem. 2002, 80, 801-812.
9. D. J. Owen, D. VanDerveer, G. B. Schuster, J. Am. Chem. Soc. 1998, 120, 1705-1717.
10. a) S. Toyota, T. Hakamata, N. Nitta, F. Ito, Chem. Lett. 2004, 33, 206-208;
11. b) S. Toyota, F. Ito, N. Nitta, T. Hakamata, Bull. Chem. Soc. Jpn. 2004, 77, 2081-2088;
12. c) S. Toyota, F. Ito, T. Yamamoto, H. Akashi, T. Iwanaga, Bull. Chem. Soc. Jpn. 2006, 79, 796-798.
13. T. Imamoto, H. Morishita, J. Am. Chem. Soc. 2000, 122, 6329-6330.
14. L. Charoy, A. Valleix, L. Toupet, T. Le Gall, P. Pham van Chuong, C. Mioskowski, Chem. Commun. 2000, 2275-2276.
15. M. Braun, R. Fleischer, B. Mai, M.-A. Schneider, S. Lachenicht, Adv. Synth. Catal. 2004, 346, 474-482.
16. M. Braun, A. Hahn, M. Engelmann, R. Fleischer, W. Frank, C. Kryschi, S. Haremza, K. Kürschner, R. Parker, Chem. Eur. J. 2005, 11, 3405-3412.
17. In a low-temperature 1H NMR spectrum (223 K) of 7a (H instead of Cl), one of the geminal phenyl rings displayed a set of five anisochronous protons (ABCDE system), indicating their hindered rotation.
18. S. Jones, C. Smanmoo, Tetrahedron Lett. 2004, 45, 1585-1588;
19. M. Murakata, H. Tsutsui, O. Hoshino, Org. Lett. 2001, 3, 299-302.
20. H. Höpfl, J. Organomet. Chem. 1999, 581, 129-149. Slightly different values resulted, when the tetrahedral character was calculated according to Ōki's equation, which is based on the three angles between boron and the covalently bound neighbouring atoms: 10a: 74%, 10b: 77%, 10c: 74%;
21. cf.: S. Toyota, M. Ōki, Bull. Chem. Soc. Jpn. 1992, 65, 1832-1840.
22. TURBOMOLE (vers. 5.8): R. Ahlrichs, M. Bär, H.-P. Baron, R. Bauernschmitt, S. Böcker, M. Ehrig, K. Eichkorn, S. Elliott, F. Furche, F. Haase, M. Häser, H. Korn, C. Huber, U. Huniar, M. Kattannek, C. Kölmel, M. Kollwitz, K. May, C. Ochsenfeld, H. Öhm, A. Schäfer, U. Schneider, O. Treutler, M. von Arnim, F. Weigend, P. Weis, H. Weiss, University of Karlsruhe 2006, siehe http://www.turbomole.com.
23. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865-3868.
24. S. Grimme, J. Comput. Chem. 2006, 27, 1787-1799.
25. A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571-2577.
26. a) R. Bauernschmitt, R. Ahlrichs, Chem. Phys. Lett. 1996, 256, 454-464;
27. b) F. Furche, R. Ahlrichs, C. Wachsmann, E. Weber, A. Sobanski, F. Vögtle, S. Grimme, J. Am. Chem. Soc. 2000, 122, 1717-1724;
28. c) C. Diedrich, S. Grimme, J. Phys. Chem. A 2003, 107, 2524-2539.
29. A. D. Becke, J. Chem. Phys. 1993, 98, 1372-1377