Salen-derived catalysts containing secondary basic groups in the addition of diethylzinc to aldehydes

Organic Letters

Volumn 3, Issue 19, 2001, Pages 3053-3056

  DiMauro, Erin F ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; ETHYLENEDIAMINE DERIVATIVE; LIGAND; METALLOPROTEIN; METALLOPROTEINASE; N,N' DISALICYLIDENEETHYLENEDIAMINE; ORGANOMETALLIC COMPOUND; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ALDEHYDES; AMINES; CATALYSIS; ETHYLENEDIAMINES; LIGANDS; METALLOENDOPEPTIDASES; METALLOPROTEINS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; ZINC;

EID: 0035922347     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016535u     Document Type: Article

References (51)

1. (a) Murthy, N. N.; Mahroof-Tahir, M.: Karlin, K. D. J. Am. Chem. Soc. 1993, 115, 10404-10405.
2. (b) Pessiki, P. J.; Dismukes, G. C. J. Am. Chem. Soc. 1994, 116, 898-903.
3. (c) Gobel, M. W. Angew. Chem., Int. Ed. 1994, 33, 1141-1143.
4. (d) Young, M. J.; Chin, J. J. Am. Chem. Soc. 1995, 117, 10577-10578.
5. (e) Kodera, M.; Shimakoshi, H.; Kano, K. Chem. Commun. 1996, 1737-1738.
6. For reviews, see: (a) Sawumura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871.
7. (b) Steinhagen, H.: Helmchen, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2339-2342.
8. (c) van den Beuken, E. K.; Ferringa, B. L. Tetrahedron 1998, 54, 12985-13011.
9. (d) Rowlands, G. J. Tetrahedron 2001, 57, 1865-1882.
10. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553.
11. (b) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071-6072.
12. (c) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
13. (d) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207-217.
14. (e) Ooi, T.; Kondo, Y.; Maruoka, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1183-1184.
15. (f) Sibi, M. P.; Cook, G. R.; Liu, P. Tetrahedron Lett. 1999, 40, 2477-2480.
16. (g) Puigjaner, C.; Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1999, 64, 7902-7911.
17. (h) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Chem. Pharm. Bull. 2000, 48, 1586-1592.
18. (i) Hamashima, Y.: Sawada, D.; Nogami, H.; Kanai, M.; Shibasaki, M. Tetrahedron, 2001, 57, 805-814.
19. (j) Gamble, M. P.; Smith, A. R. C.; Wills, M. J. Org. Chem, 1998, 63, 6068-6071.
20. DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2001, 3, 1641-1644.
21. A few examples of chiral salens with secondary functional groups have been reported. Phosphines: (a) Quirmbach, M.; Kless, A.; Holz, J.; Tararov, B.; Börner, A. Tetrahedron: Asymmetry 1999, 10, 1803-1811.
22. (b) Kless, A.; Kadyrov, R.; Börner, A.; Holz, J.; Kagan, H. B Tetrahedron Lett. 1995, 36, 4601-4602. Phenol ethers:
23. (c) Keller, F.; Rippert, A. J. Helv. Chim. Acta 1999, 82, 125-137.
24. For a recent review, see: (a) Pu, L.; Yu, H. Chem. Rev. 2001, 101, 757-824.
25. (b) Soai, K.; Shibata, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; pp 911-922.
26. 2Zn addition to aldehydes, see ref 5c and the following: Cozzi, P. G.; Papa, A.; Umani-Ronchi, A. Tetrahedron Lett. 1996, 37, 4613-4616.
27. 2Zn additions with binaphthyl-3, 3′-dicarboxamides. See ref 3d.
28. (a) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1321-1323.
29. (b) Seebach, D.; Beck, A. K.; Schmidt, B.; Wang, Y. M. Tetrahedron 1994, 50, 4363-4384.
30. (c) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1998, 30, 7095-7098.
31. (d) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691-5700.
32. (e) Pritchett, S.; Woodmansee, D. H.; Gantzel, P.; Walsh, P. J. J. Am. Chem. Soc: 1998, 720, 6423-6424.
33. (f) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem., Int. Ed. 2001, 40, 92-138.
34. (a) Liable-Sands, L. M.; Incarvito, C.; Rheingold, A. L.; Qin, C. J.; Gavrilova, A. L.; Bosnich, B. Inorg. Chem. 2001, 40, 2147-2155.
35. (b) Adams, H.; Fenton, D. E.; Haque, S. R.; Heath, S. L.; Ohba, M. J. Chem. Soc., Dalton Trans. 2000, 1849-1856.
36. (c) De Angelis, S.; Solari, E.; Gallo, E.; Floriani; C.; Chiesi-Villa, A.; Rizzoli, C. Inorg. Chem. 1996, 35, 5995-6003.
37. (d) Karunakaran, S.; Kandaswamy, M. J. Chem. Soc., Dalton Trans. 1995, 1851-1855.
38. (a) Tasker, P. A.; White, D. J. Eur. Pat. WO0058225, 2000.
39. (b) Miller, H. A., Laing, N.; Parsons, S.; Parkin, A.; Tasker, P. A.; White, D. J. J. Chem. Soc., Dalton Trans. 2000, 3773-3782.
40. (c) White, D. J.; Laing, N.; Miller, H. A.; Parsons, S.; Coles, S.; Tasker, P. A. Chem. Commun. 1999, 2077-2078.
41. Ligands 8 and 15 have previously been synthesized in racemic form: see ref 11.
42. See Supporting Information.
43. 2Zn tor 1 h at room temperature prior to the addition of substrates.
44. A reversal in facial selectivity was observed for this catalyst, which may indicate a different binding mode of the lignad or substrates for this case or an alternate mechanism.
45. 4 for 1 h.
46. For a previous synthesis of ligand 16, see: Lam, F.; Xi Xu, J.; Shing Chan, K. J. Org. Chem. 1996, 61, 8414-8418.
47. 2Zn to PhCHO using a different set of conditions. To obtain good yields, reaction temperatures of 0°C or room temperature were required.
48. Using 10 mol % of catalyst at -35°C over 15 h, the following data were collected: 9% conversion, 83% ee; 47% conversion, 85% ee; 81% conversion; 86% ee; 94% conversion, 87% ee.
49. In reactions performed using the same conditions, the following selectivities were observed for PhCHO at 97% conversion: 100% ee 8, 76% ee product; 50% ee 8, 37% ee product.
50. In a direct comparison (2 mol %, 0°C), the Zn complex of 8 was found to be at least 3-fold more reactive than the DAIB (see ref 3b-c, 6) or MIB (Nugent, W. Chem. Commun. 1999, 1369-1370) zinc complexes.
51. In a direct comparison (2 mol %, 0°C), the Zn complex of 8 was found to be at least 3-fold more reactive than the DAIB (see ref 3b-c, 6) or MIB (Nugent, W. Chem. Commun. 1999, 1369-1370) zinc complexes.