Mechanistic investigation into the addition of diethylzinc to aromatic aldehydes catalyzed by chiral o-hydroxyaryldiazaphosphonamides

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2105-2109

  Legrand, Olivier ^a   Brunel, Jean Michel ^a   Buono, Gérard ^a  

^a Ecole Centrale Marseille   (France)

Author keywords

Aromatic aldehyde; Diethylzinc; Enantioselective alkylation; Non linear effect; O hydroxyaryldiazaphosphonamide

Indexed keywords

ALDEHYDE; DIETHYLZINC; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 0034719855     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00110-6     Document Type: Article

References (31)

1. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994; Chapter 5.
2. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
3. For recent examples, see: (a) Bringmann, G.; Breuning, M. Tetrahedron: Asymmetry 1998, 9, 667-679.
4. (b) Tae Cho, B.; Sung Chun, Y. Tetrahedron: Asymmetry 1998, 9, 1489-1492.
5. © Aurich, H. G.; Soeberdt, M. Tetrahedron Lett. 1998, 39, 2553-2554.
6. (d) Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970-4982.
7. (e) Solà L.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron: Asymmetry 1997, 8, 1559-1568.
8. (f) Wilken, J.; Gröger, H.; Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1997, 8, 2761-2771.
9. (g) Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391-1401.
10. (h) Bolm, C.; Fernandez, K. M.; Seger, A.; Raabe, G. Synlett 1997, 1051-1052.
11. (i) Zhang, H.; Xue, F.; Mark, T. C. W.; Chan, K. S. J. Org. Chem. 1996, 61, 8002-8003.
12. (a) Anderson, J. C.; Harding, M. J. Chem. Soc., Chem. Commun. 1998, 393-394.
13. (b) Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1998, 9, 1409-1417.
14. Asami, M.; Inoue, S. Bull. Chem. Soc. Jpn. 1997, 70, 1687-1690.
15. Williams, D. R.; Fromhold, M. G. Synlett 1997, 523-524.
16. Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207-217.
17. (a) Legrand, O.; Brunel, J. M.; Constantieux, T.; Buono, G. Chem. Eur. J. 1998, 4, 1061-1067.
18. (b) Legrand, O.; Brunel, J. M.; Buono, G. Eur. J. Org. Chem. 1999, 1099-1105.
19. © Legrand, O.; Brunel, J. M.; Buono, G. Tetrahedron 2000, 56, 285-293.
20. (a) Brunel, J. M.; Constantieux, T.; Legrand, O.; Buono, G. Tetrahedron Lett. 1998, 39, 2961-2964.
21. (b) Legrand, O.; Brunel, J. M.; Buono, G. Tetrahedron Lett. 1998, 39, 9419-9422.
22. 4, filtered and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography on a silica gel column (eluent: diethylether:pentane 50:50) to afford the corresponding pure 1-phenyl propanol.
23. 1 from the systemic absences. A total of 1724 reflections were collected at T=298 K. The standards were measured after every 120 reflections. Among the first 200 pairs of reflections, the signs of the corresponding calculated differences, establishing that the molecule is described with the correct absolute configuration S. CCDC138892.
24. (a) Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264-4268.
25. (b) Kitamura, M.; Yamakawa, M.; Oka, H.; Suga, S.; Noyori, R. Chem. Eur. J. 1996, 2, 1173-1181.
26. (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2922-2959.
27. (b) Puchot, C.; Samuel, O.; Dunach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357.
28. (a) Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
29. (b) Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69.
30. © Kitamura, M.; Suga, S.; Niwa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 4832-4842.
31. (d) Knochel, P.; Singer, R. D. Chem. Rev. 1993, 93, 2117.