Efficient asymmetric addition of diethylzinc to ketones using tartaric acid derivative as chiral ligand

Arkivoc

Volumn 2008, Issue 2, 2008, Pages 25-32

  Hui, Ailing ^a   Zhang, Jintang ^b   Sun, Huayin ^b   Wang, Zhiyong ^b  

^a HEFEI UNIVERSITY OF TECHNOLOGY   (China)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Aldehyde; Asymmetric addition; Diethylzinc; Ketone; Tartaric acid

Indexed keywords

EID: 38349149274     PISSN: 1551-7012     EISSN: 15517012     Source Type: Journal    
DOI: 10.3998/ark.5550190.0009.204     Document Type: Article

References (28)

1. (a) Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757.
2. (b) Pu, L. Tetrahedron 2003, 59, 9873.
3. (c) Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2004, 43, 284.
4. (d) Betancort, J. M.; García, C.; Walsh, P. J. Synlett 2004, 749.
5. (a) Yoshioka, M.; Kawakita, T.; Ohno, M. Tetrahedron Lett. 1989, 30, 1657.
6. (b) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095.
7. (c) Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691.
8. (d) Pritchett, S.; Woodmansee, D. H.; Walsh, P. J. J. Am. Chem. Soc. 1998, 120, 6423.
9. (e) Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 3250.
10. (f) Balsells, J.; Betancort, J. M.; Walsh, P. J. Angew. Chem., Int. Ed. 2000, 39, 3428.
11. (g) Zhang, X. M.; Guo, C. Tetrahedron Lett. 1995, 36, 4947.
12. (h) Qiu, J.; Guo, C.; Zhang. X. M. J. Org. Chem. 1997, 62, 2665.
13. (a) García, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970.
14. (b) Yus, M.; Ramón, D. J.; Prieto, O. Tetrahedron: Asymmetry 2002, 13, 2291.
15. (c) Yus, M.; Ramón, D. J.; Prieto, O. Eur. J. Org. Chem. 2003, 2745.
16. (d) García, C.; Walsh, P. J. Org. Lett. 2003, 5, 3641.
17. (e) Prieto, O.; Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 2003, 14, 1955.
18. (f) Yus, M.; Ramón, D. J.; Prieto, O. Tetrahedron: Asymmetry 2003, 14, 1103.
19. (g) de Parrodi, C. A.; Walsh, P. J. Synlett 2004, 2417.
20. (h) Forrat, V. J.; Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 2005, 16, 3341.
21. (i) Jeon, S. J.; Li, H. M.; García, C.; LaRochelle, L. K.; Walsh, P. J. J. Org. Chem. 2005, 70, 448.
22. (j) Jeon, S. J.; Li, H. M.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 16416.
23. (a) Hui, A. L.; Zhang, J. T.; Fan, J. M.; Wang, Z. Y. Tetrahedron: Asymmetry 2006, 17, 2101.
24. (b) Hui, A. L.; Zhang, J. T.; Wang, Z. Y. Synth. Commun. 2007, accepted.
25. Terfort, A. Synthesis 1992, 951.
26. (a) Kuppert, D.; Sander, J.; Roth, C.; Worle, M.; Weyhermuller, T.; Reiss, G. J.; Schilde, U.; Muller, I.; Hegetschweiler, K. Eur. J. Inorg. Chem. 2001, 2525.
27. (b) Slarżewski, J.; Gupta, A. Tetrahedron: Asymmetry 1997, 8, 1861.
28. You, J. S.; Shao, M. Y.; Gau, H. M. Tetrahedron: Asymmetry 2001, 12, 2971.