Reversal of stereochemistry in diethylzinc addition to aldehydes by a simple change of the backbone substituent in L-serine derived ligands

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3301-3304

  Sibi, Mukund P ^a   Chen, Jian xie ^a   Cook, Gregory R ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

Diethylzinc; Enantioselective Addition; Serine

Indexed keywords

ALDEHYDE; LIGAND; SERINE;

ARTICLE; CATALYSIS; CHIRALITY; CONFORMATIONAL TRANSITION; ENANTIOMER; LIGAND BINDING; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0033597270     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00480-3     Document Type: Article

References (41)

1. 1. For a comprehensive review see: Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
2. 2. For some recent work see: (a) Vyskocil, S.; Jaracz, S.; Smrcina, M.; Stícha, M.; Hanus, V.; Polasek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7727.
3. (b) Anderson, J. C.; Cubbon, R.; Harding, M.; James, D. J. Tetrahedron: Asymmetry 1998, 9, 3461.
4. (c) Asami, M.; Watanabe, H.; Honda, K.; Inoue, S. Tetrahedron: Asymmetry 1998, 9, 4165.
5. (d) Qiu, J.; Guo, C.; Zhang, X. J. Org. Chem. 1997, 62, 2665.
6. 3. (a) Jones, G. B.; Guzel, M.; Chapman, B. J. Tetrahedron: Asymmetry 1998, 9, 901.
7. (b) Bolm, C.; Muñiz-Fernández, K.; Seger, A.; Raabe, G.; Günther, K. J. Org. Chem. 1998, 63, 7860.
8. (c) Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry 1998, 9, 2595.
9. 4. (a) Huang, W.-S.; Hu, Q.-S.; Pu, L. J. Org. Chem. 1998, 63, 1364.
10. (b) Soai, K.; Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97.
11. (c) Itsuno, S.; Sakurai, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Frechet, J. M. J. J. Org. Chem. 1990, 55, 304.
12. (d) Vidal-Ferran, A.; Bampos, N.; Moyano, A.; Pericas, M.; Riera, A.; Sanders, J. K. M. J Org. Chem. 1998, 63, 6309.
13. 5. For a comparison of various ligands see: Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078.
14. 6. (a) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530.
15. (b) Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391.
16. (c) Oppolzer, W.; Radinov, R. N. Tetrahedron Lett. 1988, 29, 5645.
17. (d) Zhu, H-J.; Zhao, B-T.; Dai, W-M.; Zhou, J.; Hao, X-J. Tetrahedron: Asymmetry 1998, 9, 2879.
18. (e) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529.
19. (f) Dai, W-M.; Zhu, H. J.; Hao, X-J. Tetrahedron: Asymmetry 1995, 6, 1857.
20. (g) Chelucci, G.; Berta, D.; Fabbri, D.; Pinna, G. A.; Saba, A.; Ulgheri, F. Tetrahedron: Asymmetry 1998, 9, 1933.
21. (h) Williams, D. R.; Fromhold, M. G. Synlett 1997, 523.
22. 7. For reactions with cysteine derived ligands see: (a) Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1998, 9, 1409.
23. (b) Kossenjans, M.; Pennemann, H.; Martens, J. Juanes, O.; Rodriguez-Ubis, J. C.; Brunet, E. Tetrahedron: Asymmetry 1998, 9, 4123.
24. 8. Soai, K.; Watanabe, M.; Yamamoto, A.; Yamashita, T. J. Mol. Cat. Lett. 1991, 64, L27.
25. 9. For the use of aliphatic side chains see: (a) Delair, P.; Einhorn, C.; Einhorn, J.; Luche, J. L. Tetrahedron 1995, 51, 165.
26. (b) Beliczey, J.; Giffels, G.; Kragl, U.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1529.
27. (c) Ref. 6f.
28. 10. All new compounds showed analytical characteristics consistent with their structure.
29. 11. The lithium alkoxides of 2 and 3 did not provide improved selectivity 2 gave 35% yield and 19%ee (S) and 3 gave 26% yield and 10% ee (S).
30. 12. (a) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233 and 5237.
31. (b) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49.
32. (c) Refs. 1 and 2a.
33. (d) Soai, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111.
34. (e) de Vries, E. F. J.; Brussee, J.; Kruse, C. C.; van der Gen, A. Tetrahedron: Asymmetry 1993, 4, 1987.
35. (f) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970.
36. (g) Mehler, T.; Martens, J. Tetrahedron: Asymmetry 1994, 5, 207.
37. 13. (a) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
38. (b) Refs. 1, 2a, 12a, 12d.
39. (c) Watanabe, M.; Araki, S.; Butsugan, Y.; Uemura, M. J. Org. Chem. 1991, 56, 2218.
40. (d) Goldfuss, B.; Houk, K. N. J. Org. Chem. 1998, 63, 8998.
41. (e) Yamakawa, M.; Noyori, R. Organometallics 1999, 18, 128.