Single enantiomer, chiral donor-acceptor metal complexes from bisoxazoline pseudoracemates

Organic Letters

Volumn 8, Issue 13, 2006, Pages 2759-2762

  Atkins, Jeffery M ^a   Moteki, Shin A ^a   DiMagno, Stephen G ^a   Takacs, James M ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; OXAZOLE DERIVATIVE; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXAZOLES; STEREOISOMERISM; ZINC;

EID: 33746119199     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060836s     Document Type: Article

References (34)

1. Takacs, J. M.; Hrvatin, P. M.; Atkins, J. M.; Reddy, D. S.; Clark, J. L. New J. Chem. 2005, 29, 263-265.
2. The combinatorial synthesis of chiral self-assembled ligands for asymmetric catalysis via the box-directed coupling of bifunctional ligands is an ongoing application of this strategy. See: Takacs, J. M.; Reddy, D. S.; Moteki, S. A.; Wu, D.; Palencia, H. J. Am. Chem. Soc. 2004, 126, 4494-4495.
3. Takacs, J. M.; Chaiseeda, K.; Moteki, S. A.; Reddy, D. S.; Wu, D.; Chandra, K. Pure Appl. Chem. 2006, 78, 501-509.
4. Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21-38.
5. Di Bella, S. Chem. Soc. Rev. 2001, 30, 355-366.
6. de la Torre, G.; Vazquez, P.; Agullo-Lopez, F.; Torres, T. Chem. Rev. 2004, 104, 3723-3750.
7. Coe, B.; Curati, N. Comments Inorg. Chem. 2004, 25, 147-184.
8. Rechavi, D.; Lemaire, M. Chem. Rev. 2002, 102, 3467-3493.
9. Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001-4004.
10. Kwak, Y.-S.; Corey, E. J. Org. Lett. 2004, 6, 3385-3388.
11. Choi, H.-W.; Demeke, D.; Kang, F.-A.; Kishi, Y.; Nakajima, K.; Nowak, P.; Wan, Z.-K.; Xie, C. Pure Appl. Chem. 2003, 75, 1-17.
12. Ward, D. E.; Sales, M.; Hrapchak, M. J. Can. J. Chem. 2001, 79, 1775-1785.
13. Dagorne, S.; Bellemin-Laponnaz, S.; Welter, R. Organometallics 2004, 23, 3053-3061.
14. Bayardon, J.; Sinou, D. J. Org. Chem. 2004, 69, 3121-3128.
15. Zhou, J.; Ye, M.-C.; Tang, Y. J. Comb. Chem. 2004, 6, 301-304.
16. Zhou, J.; Tang, Y. Chem. Commun. 2004, 432-433.
17. Bourguignon, J.; Bremberg, U.; Dupas, G.; Hallman, K.; Hagberg, L.; Hortala, L.; Levacher, V.; Lutsenko, S.; Macedo, E.; Moberg, C.; Queguiner, G.; Rahm, F. Tetrahedron 2003, 59, 9583-9589.
18. Sibi, M. P.; Chen, J. Org. Lett. 2002, 4, 2933-2936.
19. Bellemin-Laponnaz, S.; Gade, L. H. Angew. Chem., Int. Ed. 2002, 41, 3473-3475.
20. Burguete, M. I.; Fraile, J. M.; Garcia, J. I.; Garcia-Verdugo, E.; Herrerias, C. I.; Luis, S. V.; Mayoral, J. A. J. Org. Chem. 2001, 66, 8893-8901.
21. Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Eur. J. Org. Chem. 2001, 1045-1048.
22. Denmark, S. E.; Stiff, C. M. J. Org. Chem. 2000, 65, 5875-5878.
23. Schulze, V.; Hoffmann, R. W. Chem.-Eur. J. 1999, 5, 337-344.
24. Uno, M.; Seto, K.; Masuda, M.; Ueda, W.; Takahashi, S. Tetrahedron Lett. 1985, 26, 1553-1556.
25. Gao, C.; Tao, X.; Qian, Y.; Huang, J. Chem. Commun. 2003, 1444-1445 and references therein.
26. Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173-1180.
27. Makarycheva-Mikhailova, A. V.; Kukushkin, V. Y.; Nazarov, A. A.; Garnovskii, D. A.; Pombeiro, A. J. L.; Haukka, M.; Keppler, B. K.; Galanski, M. Inorg. Chem. 2003, 42, 2805-2813 and references therein.
28. Abbotto, A.; Bradamante, S.; Facchetti, A.; Pagani, G. A. J. Org. Chem. 2002, 67, 5753-5772.
29. Suzuki, H.; Koide, H.; Ogawa, T. Bull. Chem. Soc. Jpn. 1988, 61, 501-504.
30. Leader, H.; Smejkal, R. M.; Payne, C. S.; Padilla, F. N.; Doctor, B. P.; Gordon, R. K.; Chiang, P. K. J. Med. Chem. 1989, 32, 1522-1528.
31. Saalfrank, R. W.; Struck, O.; Peters, K.; Georg von Schnering, H. Z. Naturforsch., B: Chem. Sci. 1994, 49, 1415-1424.
32. Yang, J.-S.; Lin, Y.-D.; Lin, Y.-H.; Liao, F.-L. J. Org. Chem. 2004, 69, 3517-3525.
33. Lin, V. S. Y.; Therien, M. J. Chem.-Eur. J. 1996, 1, 645-651.
34. 3) leads to a near statistical 2.7:1:1 mixture of DA complex (RR,SS)-5e and the two starting complexes, again suggesting that DA interaction in the ground state is weak.