Highly catalytic asymmetric addition of deactivated alkyl Grignard reagents to aldehydes

Organic Letters

Volumn 11, Issue 24, 2009, Pages 5578-5581

  Da, Chao Shan ^a,b   Wang, Jun Rul ^a   Yin, Xiao Gang ^a   Fan, Xin Yuan ^a   Liu, Yi ^a   Yu, Sheng Li ^a  

^a Sch Life Sci Bharathidasan U   (India)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BINOL, NAPHTHOL; BIS(2 (DIMETHYLAMINO)ETHYL) ETHER; BIS(2-(DIMETHYLAMINO)ETHYL) ETHER; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ETHER DERIVATIVE; NAPHTHOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; ETHYL ETHERS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; NAPHTHOLS; STEREOISOMERISM;

EID: 72849128746     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9020942     Document Type: Article

References (53)

1. (a) Wakefield. B. J., Ed. Organomagnesium Methods in Organic Synthesis: Academic Press: San Diego. CA, 1995.
2. (b) Franzén, R. G. Tetrahedron 2000, 56, 685.
3. (c) Richey, H. G.. Ed. New Developments: Grignard Reagents; Wiley: Chichester, UK, 2000.
4. (d) López, F.; Minnaard, A. J.; Feringa, B. L. Acc. Chem. Res. 2007, 40, 179.
5. (e) Luderer, M. R.; Bailey, W. F.; Luderer. M. R.; Fair, J. D.; Dancer. R. J.; Sommer. M. B. Tetrahedron: Asymmetry 2009, 20, 981.
6. (a) Weber, B.; Seebach, D. Angew. Chem., Int. Ed. 1992, 31, 84.
7. (b) Weber. B.; Seebach, D. Tetrahedron 1994, 50, 6117.
8. (c) Mukaiyama, T.; Soai, K.; Sato, T.; Shimizu, H.; Suzuki. K. J. Am. Chem. Soc. 1979, 101, 1455.
9. (d) Nakajima, M.; Tomioka, K.; Koga. K. Tetrahedron 1993, 49, 9751.
10. (e) Yong. K. H.; Taylor, N. J.; Chong. J. M. Org. Lett. 2002, 4, 3553.
11. (f) Rozema, M. J.; Fickes, M.; McLaughlin, M.; Rohde, B.; McDermotte. T. Tetrahedron Lett. 2006, 47, 8767.
12. (g) Pritchett. S.; Woodmansee, D. H.; Gantzel, P.; Walsh, P. J. J. Am. Chem. Soc. 1998, 120, 6423.
13. (a) Cohen, H. L.; Wright. G. F. J. Org. Chem. 1953, 18, 432.
14. (b) Seebach, D.; Dorr, H.; Bastani, B.; Ehrig. V. Angrew. Chem., Int. Ed. 1969, 8, 982.
15. (c) Seebach. D.; Langer, W. Helv. Chim. Acta 1979, 62, 1701.
16. (a) Pu. L.; Yu. H. Chem. Rev. 2001, 101, 757.
17. (b) Da, C.-S.; Ni, M.; Han, Z.-J.; Yang. F.; Wang. R. J. Mol. Catal. A: Chem. 2006, 245, 1.
18. (c) Da, C.-S.; Han. Z.-J.; Ni, M.; Yang, F.; Liu, D.-X.; Zhou. Y.-F.; Wang, R. Tetrahedron: Asymmetry 2003, 14, 659.
19. (d) Nugent. W. A. Org. Lett. 2002, 4, 2133.
20. (e) Chen, Y. K.; Costa, A. M.; Walsh. P. J. J. Am. Chem. Soc. 2001, 123, 5378.
21. (f) Huang, W. S.; Hu. Q. S.; Pu, L. J. Org. Chem. 1998, 63, 1364.
22. (g) Soai, K.; Ookawa. A.; Kaba. T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111.
23. (h) Kitamura, M.; Okada. S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
24. (a) Noyori. R.; Hashiguchi. S. Acc. Chem. Res. 1997, 30, 97.
25. (b) Cho, B. T. Chem. Soc. Rev. 2009, 38, 443.
26. (c) Ikariya, T.; Blacker. A. J. Acc. Chem. Res. 2007, 40, 1300.
27. (d) Genet, J.-P. Acc. Chem. Res. 2003, 36, 908.
28. (e) Tang. W.; Zhang. X. M. Chem. Rev. 2003, 103, 3029.
29. (f) Corey, E. J.; Helal. C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.
30. (a) Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem., Int. Ed. 1991, 30, 1008.
31. (b) Von Dem Bussche-Hünnefeld, J. L.; Seebach. D. Tetrahedron 1992, 48, 5719.
32. (c) Côté. A.; Charette. A. B. J. Am. Chem. Soc. 2008, 130, 2771.
33. (d) Soai. K.; Kawase. Y.; Oshio, A. J. Chem. Soc., Perkin Trans. 1 1991, 1613.
34. (e) Soai, K.; Kawase, Y. J. Chem. Soc., Perkin Trans. 1 1990, 3214.
35. (a) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807.
36. (b) Yang. X.-W.; Shen, J.-H.; Da, C.-S.; Wang, H.-S.; Su, W.; Wang, R.; Chan, A. S. C. J. Org. Chem. 2000, 65, 295.
37. (c) Wu, K.; Gau, H. J. Am. Chem. Soc. 2006, 128, 14808.
38. (d) Balsells, J.; Davis, T. J.; Carroll, P.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10336.
39. (a) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473.
40. (b) Muramatsu, Y.; Harada, T. Angew. Chem., Int. Ed. 2008, 47, 1088.
41. (c) Muramatsu, Y.; Harada, T. Chem-Eur. J. 2008, 14, 10560.
42. (a) Li, H.; Da, C.-S.; Xiao, Y.-H.; Li, X.; Su, Y.-N. J. Org. Chem. 2008, 73, 7398.
43. (b) Saito, S.; Yamamoto, H. Acc. Chem. Res. 2004, 37, 570.
44. (c) Trost, B. M.; Hitce, J. J. Am. Chem. Soc. 2009, 131, 4572.
45. (d) Lu, G.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. Angew. Chem, Int. Ed. 2008, 47, 7714.
46. (e) Jiang, H.; Falcicchio, A.; Jensen, K. L.; Paixão, M. W.; Bertelsen, S.; Jørgensen, K. A. J. Am. Chem. Soc. 2009, 131, 7153.
47. Wang, X.; Zhang, L.; Sun, X.; Xu, Y.; Krishnamurthy, D.; Senananyaka, C. H. Org. Lett. 2005, 7, 5593.
48. (a) Rudolph, J.; Hermanns, N.; Bolm, C. J. Org. Chem. 2004, 69, 3997.
49. (b) Schmidt, F.; Stemmler, R. T.; Rudolph, J.; Bolm, C. Chem. Soc. Rev. 2006, 35, 454.
50. (c) Kim. J. G.; Walsh, P. J. Angew. Chem., Int. Ed. 2006, 45, 4175.
51. (d) Salvi, L.; Jeon. S.; Fisher. E. L.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2007, 129, 16119.
52. (e) Salvi, L.; Kim, J. G.; Walsh, P. J. J. Am. Chem. Soc. 2009, 131, 12483.
53. (f) Shannon, J.; Bernier, D.; Rawson. D.; Woodward, S. Chem. Commun. 2007, 3945.