Crystal structures of (+)-sparteine surrogate adducts of methyllithium and phenyllithium

Organometallics

Volumn 23, Issue 23, 2004, Pages 5389-5391

  Strohmann, Carsten ^a   Strohfeldt, Katja ^a   Schildbach, Daniel ^a   McGrath, Matthew J ^b   O'Brien, Peter ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; ANISOTROPY; COMPUTATIONAL METHODS; DIMERS; MOLECULAR STRUCTURE; OPTIMIZATION;

ADDUCTS; ASYMMETRIC SYNTHESIS; DEPROTONATION; DIFFRACTION ANGLES;

CRYSTAL STRUCTURE;

EID: 9144250362     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0494871     Document Type: Article

References (31)

1. In general, we speak of enantiomerically enriched alkyllithiums when we focus on the stereogenic lithiated carbon center. In reality, such alkyllithiums are almost always diastereomerically enriched.
2. (a) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. 1997, 36, 2282.
3. (b) Basu, A.; Thayumanavan, S. Angew. Chem., Int. Ed. 2002, 41, 716.
4. Pippel, D. J.; Weisenburger, G.; Wilson, S. R.; Beak, P. Angew. Chem., Int. Ed. 1998, 37, 2522.
5. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
6. (a) Alexakis, A.; Vrancken, E.; Mangeney, P. Synlett 1998, 11, 1165.
7. (b) Norsikian, S.; Marek, I.; Klein, S.; Poisson, J. F.; Normant, J. F. Chem. Eur. J. 1999, 5, 2055.
8. (c) Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. J. Am. Chem. Soc. 1994, 116, 8797.
9. (a) Strohmann, C.; Seibel, T.; Strohfeldt, K. Angew. Chem., Int. Ed. 2003, 42, 4531.
10. (b) Strohmann, C.; Strohfeldt, K.; Schildbach, D. J. Am. Chem. Soc. 2003, 125, 13672.
11. (c) Strohfeldt, K.; Schildbach, D.; Seibel, T.; Strohmann, C. 3rd International Conference on the Chemistry of Alkali and Alkaline Earth Metals, Alkchem-3; Würzburg, Germany, 2003; Poster No. P03.
12. (d) Vestergren, M.; Eriksson, J.; Hilmersson, G.; Håkansson, M. J. Organomet. Chem. 2003, 682, 172.
13. -1) was added. The mixture was warmed to -30°C over 12 h. Colorless block-shaped single crystals of compound 3 were obtained.
14. 2) = 0.1221 (all data).
15. Due to the lack of heavy atoms, the Flack parameter (or absolute structure factor), which usually indicates the refinement of the absolute structure, is not significant for each of the crystal structures reported. Therefore, it is neither listed nor discussed (see also: Flack, H. D.; Bernardinelli, G. J. Appl. Crystallogr. 2000, 33, 1143). Nevertheless, the refinement of the absolute structure is unambiguous, on account of the fixed absolute configurations at the chiral ligands (determination of the relative configuration). For the absolute and relative stereochemistry of (-)-l see refs 2a and 11b; for (-)-2 see ref 12a,b.
16. Keller, E. Schakal99; University of Freiburg, Freiburg, Germany, 1999.
17. (a) Ebner, T.; Eichelbaum, M.; Fischer, P.; Meese, C. O. Arch. Pharm. 1989, 322, 399.
18. (b) Smith, T. B.; Wendt, J. A.; Aubé, J. Org. Lett. 2002, 4, 2577.
19. (a) Hermet, J.-P. R.; Porter, D. W.; Dearden, M. J.; Harrison, J. R.; Koplin, T.; O'Brien, P.; Parmene, J.; Tyurin, V.; Whitwood, A. C.; Gilday, J.; Smith, N. M. Org. Biomol. Chem. 2003, 1, 3977.
20. (b) Dearden, M. J.; Firkin, C. R.; Hermet, J.-P. R.; O'Brien, P. J. Am. Chem. Soc. 2002, 124, 11870.
21. (c) Harrison, J. R.; O'Brien, P.; Porter, D. W.; Smith, N. M. Chem. Commun. 2001, 1202.
22. -1) was added. The mixture was warmed to -30°C over 12 h. Colorless block-shaped single crystals of compound 4 were obtained.
23. 2) = 0.1469 (all data).
24. Stey, T.; Stalke, D. In The Chemistry of Organolithium Compounds; Rappoport, Z., Marek, I., Eds.; Wiley: Chichester, U.K., 2004; p 47, and literature cited therein.
25. (a) Wijkens, P.; Jastrzebski, J. T. B. H.; Veldman, N.; Spek, A. L.; van Koten, G. Chem. Commun. 1997, 2143.
26. (b) Dinnebier, R. E.; Behrens, U.; Olbrich, F. J. Am. Chem. Soc. 1998, 120, 1430.
27. (c) Donkervoort, J. G.; Vicario, J. L.; Rijnberg, E.; Jastrzebski, J. T. B. H.; Kooijman, H.; Spek, A. L.; van Koten, G. J. Organomet. Chem. 1998, 463, 463.
28. (d) Strohmann, C.; Abele, B. C. Organometallics 2000, 19, 4173.
29. -1) was added. The mixture was warmed to -30°C over 12 h. Colorless block-shaped single crystals of compound 4 were obtained.
30. 2) = 0.0916 (all data).
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.