Catalytic enantioselective addition of organoaluminum reagents to aldehydes

Tetrahedron Asymmetry

Volumn 23, Issue 10, 2012, Pages 789-794

  Fernández Mateos, Emilio ^a   MacIá, Beatriz ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKYL GROUP; ALUMINUM DERIVATIVE; LIGAND; METHYL GROUP; ORGANOMETALLIC COMPOUND; PROPANE; REAGENT; TITANIUM DERIVATIVE;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; METHYLATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; QUANTUM YIELD;

EID: 84862980485     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.05.007     Document Type: Article

References (58)

1. H.J. Zhu, J.X. Jiang, J. Ren, Y.M. Yan, and C.U. Pittman Curr. Org. Synth. 2 2005 547 587
2. R. Noyori, and M. Kitamura Angew. Chem., Int. Ed. Engl. 30 1991 49 69
3. F.R. Hartley, and S. Patai Carbon-Carbon Bond Formation Using Organometallic Compounds 1985 Wiley New York
4. M. Hatano, T. Miyamoto, and K. Ishihara Curr. Org. Chem. 11 2007 127 157
5. R. Noyori Asymmetric Catalysis in Organic Synthesis 1994 Wiley New York
6. C.M. Binder, and B. Singaram Org. Prep. Proced. Int. 43 2011 139 208
7. A. Lemiere, A. Côté, M.K. Janes, and A.B. Charette Aldrichim. Acta 42 2009 71 83
8. M. Yus, and D.J. Ramón Recent Res. Dev. Org. Chem. 6 2002 297 378
9. L. Pu, and H.-B. Yu Chem. Rev. 101 2001 757 824
10. S. Alegre, M. Diéguez, and O. Pàmies Tetrahedron: Asymmetry 22 2011 834 839
11. E. Raluy, M. Diéguez, and O. Pàmies Tetrahedron: Asymmetry 20 2009 1575 1579
12. K. Biswas, O. Prieto, P.J. Goldsmith, and S. Woodward Angew. Chem., Int. Ed. 44 2005 2232 2234
13. K.-H. Wu, and H.-M. Gau J. Am. Chem. Soc. 128 2006 14808 14809
14. J.-S. You, S.-H. Hsieh, and H.-M. Gau Chem. Commun. 2001 1546 1547
15. J.-F. Lu, J.-S. You, and H.-M. Gau Tetrahedron: Asymmetry 11 2000 2531 2535
16. B.L. Pagenkopf, and E.M. Carreira Tetrahedron Lett. 39 1998 9593 9596
17. A.S.C. Chan, F.-Y. Zhang, and C.-W. Yip J. Am. Chem. Soc. 119 1997 4080 4081
18. A.V.R. Madduri, S.R. Harutyunyan, and A.J. Minnaard Angew. Chem., Int. Ed. 51 2012 3164 3167
19. A.V.R. Madduri, A.J. Minnaard, and S.R. Harutyunyan Chem. Commun. 48 2012 1478 1480
20. E. Fernández-Mateos, B. Maciá, D.J. Ramón, and M. Yus Eur. J. Org. Chem. 2011 6851 6855
21. D. Itakura, and T. Harada Synlett 2011 2875 2879
22. Y. Liu, C.-S. Da, S.-L. Yu, X.-G. Yin, J.-R. Wang, X.-Y. Fan, W.-P. Li, and R. Wang J. Org. Chem. 75 2010 6869 6878
23. X.-Y. Fan, Y.-X. Yang, F.-F. Zhuo, S.-L. Yu, X. Li, Q.-P. Guo, Z.-X. Du, and C.-S. Da Chem. Eur. J. 16 2010 7988 7991
24. C.-S. Da, J.-R. Wang, X.-G. Yin, X.-Y. Fan, Y. Liu, and S.-L. Yu Org. Lett. 11 2009 5578 5581
25. Y. Muramatsu, and T. Harada Angew. Chem., Int. Ed. 47 2008 1088 1090
26. Y. Muramatsu, and T. Harada Chem. Eur. J. 14 2008 10560 10563
27. Fernández-Mateos, E.; Maciá, B.; Yus, M. Eur. J. Org. Chem. 2012, in press. http://dx.doi.org/10.1002/ejoc.201200464
28. K. Tanaka, K. Kukita, T. Ichibakase, S. Kotanib, and M. Nakajima Chem. Commun. 47 2011 5614 5616
29. B. Lecachey, C. Fressigné, H. Oulyadi, A. Harrison-Marchand, and J. Maddaluno Chem. Commun. 47 2011 9915 9917
30. F.A. Cotton, G. Wilkinson, C.A. Murillo, and M. Bochmann Advanced Inorganic Chemistry 6th ed. 1999 Wiley New York
31. G. Gao, X.-F. Bai, H.-M. Yang, J.-X. Jiang, G.-Q. Lai, and L.-W. Xu Eur. J. Org. Chem. 2011 5039 5046
32. G. Gao, F.-L. Gu, J.-X. Jiang, K. Jiang, C.-Q. Sheng, G.-Q. Lai, and L.-W. Xu Chem. Eur. J. 17 2011 2698 2703
33. S.-I. Kiyooka, T. Tsutsui, and T. Kira Tetrahedron Lett. 49 1996 8093 8904
34. The chiral methyl carbinol moiety is present in a large number of natural products and biologically active compounds. See, for example: F. Cohen, and L.E. Overman J. Am. Chem. Soc. 128 2006 2604 2608
35. G. Sabitha, C.S. Reddy, and J.S. Yadav Tetrahedron Lett. 47 2006 4513 4516
36. M.S. Scott, C.A. Luckhurst, and D.J. Dixon Org. Lett. 7 2005 5813 5816
37. G. Pattenden, D.J. Critcher, and M. Remunian Can. J. Chem. 82 2004 353 365
38. G.B. Jones, M. Guzel, and B.J. Chapman Tetrahedron: Asymmetry 9 1998 901 905
39. S. Hanessian Total Synthesis of Natural Products: The Chiron Approach 1983 Pergamon Oxford
40. M.L. Kantam, S. Laha, J. Yadav, P.R. Likhar, B. Sreedhar, S. Jha, S. Bhargava, M. Udayakiran, and B. Jagadeesh Org. Lett. 10 2008 2979 2982
41. Y. Li, Y. Zhou, Q. Shi, K. Ding, C.A. Sandoval, and R. Noyori Adv. Synth. Catal. 353 2011 495 500
42. W. Wang, and Q. Wang Chem. Commun. 46 2010 4616 4618
43. Q.-M. Zhu, D.-J. Shi, C.-G. Xia, and H.-M. Huang Chem. Eur. J. 17 2011 7760 7763
44. A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, and R. Noyori J. Am. Chem. Soc. 118 1996 2521 2522
45. J.-H. Xie, X.-Y. Liu, J.-B. Xie, L.-X. Wang, and Q.-L. Zhou Angew. Chem., Int. Ed. 50 2011 7329 7332
46. M.L. Kantam, J. Yadav, S. Laha, P. Srinivas, B. Sreedhar, and F. Figueras J. Org. Chem. 74 2009 4608 4611
47. M. Uchiyama, N. Katoh, R. Mimura, N. Yokota, Y. Shimogaichi, M. Shimazaki, and A. Ohta Tetrahedron: Asymmetry 8 1997 3467 3474
48. T. Inagaki, A. Ito, J. Ito, and H. Nishiyama Angew. Chem., Int. Ed. 49 2010 9384 9387
49. X. Zhang, Z. Lu, C. Fu, and S. Ma Org. Biomol. Chem. 7 2009 3258 3263
50. B. Erdélyi, A. Szabó, G. Seres, L. Birincsik, J. Ivanics, G. Szatzker, and L. Poppe Tetrahedron: Asymmetry 17 2006 268 274
51. B.K. Langlotz, H. Wadepohl, and L.H. Gade Angew. Chem., Int. Ed. 47 2008 4670 4674
52. R. Touati J. Soc. Chim. Tun. 10 2008 127 139
53. N.A. Salvi Tetrahedron: Asymmetry 19 2008 1992 1997
54. For racemic mixture see: B. Kuhlmann, E.M. Arnett, and M. Siskin J. Org. Chem. 59 1994 3098 3101
55. For racemic mixture see: W.H. Pearson, and W.-K. Fang J. Org. Chem. 60 1995 4960 4961
56. For racemic mixture see: M.C.P. Yeh, P. Knochel, and L.E. Santa Tetrahedron Lett. 29 1988 3887 3890
57. F. Tjosaas Arkivoc 6 2008 81 90
58. M. Kasai, C. Froussios, and H. Ziffer J. Org. Chem. 48 1983 459 464