Indolinylmethanol catalyzed enantioselective Reformatsky reaction with ketones

Tetrahedron Asymmetry

Volumn 21, Issue 23, 2010, Pages 2816-2824

  Lin, Ning ^a   Chen, Miao Miao ^a   Luo, Ren Shi ^a   Deng, Yan Qiu ^a   Lu, Gui ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC KETONE; INDOLINYLMETHANOL; KETONE; LIGAND; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CHIRALITY; POWDER; PRIORITY JOURNAL; REFORMATSKY REACTION;

EID: 78651406017     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.11.004     Document Type: Article

References (38)

1. F. Orsini, and G. Sello Curr. Org. Synth. 1 2004 111
2. A. Fürstner Synthesis 1989 571
3. R. Ocampo, and W.R. Dolbier Tetrahedron 60 2004 9325
4. C.M.R. Ribeiro, and F.M.C. de Farias Mini-Rev. Org. Chem. 3 2006 1
5. P.G. Cozzi Angew. Chem., Int. Ed. 46 2007 2568
6. J.M. Andrés, Y. Martín, R. Pedrosa, and A. Perez-Encabo Tetrahedron 53 1997 3787
7. A. Ojida, T. Yamano, N. Taya, and A. Tasaka Org. Lett. 4 2002 3051
8. P.G. Cozzi, A. Mignogna, and L. Zoli Synthesis 2007 2746
9. P.G. Cozzi Angew. Chem., Int. Ed. 45 2006 2951
10. P.G. Cozzi, A. Mignogna, and P. Vicennati Adv. Synth. Catal. 350 2008 975
11. P.G. Cozzi, F. Benfatti, M.G. Capdevila, and A. Mignogna Chem. Commun. 2008 3317
12. F. Benfatti, and P.G. Cozzi Tetrahedron: Asymmetry 21 2010 1503
13. M.Á. Fernández-Ibáñez, B. Maciá, A.J. Minnaard, and B.L. Feringa Chem. Commun. 2008 2571
14. M.Á. Fernández-Ibáñez, B. Maciá, A.J. Minnaard, and B.L. Feringa Angew. Chem., Int. Ed. 47 2008 1317
15. M.Á. Fernández-Ibáñez, B. Maciá, A.J. Minnaard, and B.L. Feringa Org. Lett. 10 2008 4041
16. T. Tanaka, and M. Hayashi Chem. Lett. 37 2008 1298
17. A.Q. Mi, Z.Y. Wang, Z.W. Chen, Y.Z. Jiang, A.S.C. Chen, and T.K. Yang Tetrahedron: Asymmetry 6 1995 2641
18. A.Q. Mi, Z.Y. Wang, J.M. Zhang, and Y.Z. Jiang Synth. Commun. 27 1997 1469
19. K. Soai, A. Oshio, and T. Saito J. Chem. Soc., Chem. Commun. 1993 811
20. R.J. Kloetzing, T. Thaler, and P. Knochel Org. Lett. 8 2006 1125
21. Y.H. Kim, D.H. Park, and I.S. Byun Heteroat. Chem. 3 1992 51
22. Y.H. Kim, D.H. Park, I.S. Byun, I.K. Yoon, and C.S. Park J. Org. Chem. 58 1993 4511
23. M. Asami, T. Suga, K. Honda, and S. Inoue Tetrahedron Lett. 38 1997 6425
24. M. Asami, and A. Seki Chem. Lett. 2002 160
25. T. Yoshida, K. Sakakibara, and M. Asami Chem. Lett. 32 2003 150
26. A. Agarkov, E.W. Uffman, and S.R. Gilbertson Org. Lett. 5 2003 2091
27. X.P. Tang, B. Liégault, J.L. Renaud, and C. Bruneau Tetrahedron: Asymmetry 17 2006 2187
28. R.S. Luo, J. Weng, H.B. Ai, G. Lu, and A.S.C. Chan Adv. Synth. Catal. 351 2009 2449
29. P.G. Cozzi, and E. Rivalta Angew. Chem., Int. Ed. 44 2005 3600
30. P.G. Cozzi, and E. Rivalta Pure Appl. Chem. 78 2006 287
31. J.C. Adrian, and M.L. Snapper J. Org. Chem. 68 2003 2143
32. A.Q. Mi, Z.Y. Wang, X.M. Zhang, F.M. Fu, and Y.Z. Jiang Acta Chim. Sinica 56 1998 719
33. S. Conti, M. Falorni, G. Giacomelli, and F. Soccolini Tetrahedron 48 1992 8993
34. 2 under similar conditions, affording the corresponding adducts in 91% yield (53% ee) and 95% yield (44% ee) respectively. It is appropriate to attribute the effect of a nickel salt as a Lewis acid.
35. M.P. Sibi, and S. Manyem Org. Lett. 4 2002 2929
36. A.R. Gholap, and A.P. Chavan J. Chem. Res., Synop. 2003 374
37. D. DeKeukeleire, and W. Saeyens Synth. Commun. 26 1996 4397
38. G.M. Sheldrick shelxl97. Program for Crystal Structure Refinement 1997 Univ. of Göttingen Göttingen (Germamy)