Chiral 8-substituted 10,10-dimethyl-5-pyridin-2-yl-6-aza-tricyclo[7.1.1. 02,7]undeca-2(7),3,5-trien-8-ols as enantioselective catalysts in the addition of diethylzinc to substituted benzaldehydes

Journal of Molecular Catalysis A: Chemical

Volumn 243, Issue 1, 2006, Pages 89-98

  Lin, Rong Xin ^a   Chen, Chinpiao ^a  

^a NATIONAL DONG HWA UNIVERSITY   (Taiwan)

Author keywords

Asymmetric alkylation; Chiral ligand; Diethylzinc; Enantiomeric excess; Enantioselective catalyst

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; ALKYLATION; ALPHA PARTICLES; CATALYST SELECTIVITY; ELECTRONS; SUBSTITUTION REACTIONS;

ASYMMETRIC ALKYLATION; CHIRAL LIGAND; DIETHYLZINC; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE CATALYST;

ALDEHYDES;

EID: 28244444560     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2005.07.047     Document Type: Article

References (92)

1. R.E. Gawley, and J. Aube Principles of Asymmetric Synthesis 1996 Pergamon London
2. M.P. Doyle Advances in Catalytic Processes 1 1995 JAI London
3. R. Noyori Asymmetric Catalysis in Organic Synthesis 1994 Wiley New York
4. H. Brunner, and W. Zettlmeier Handbook of Enantioselective Catalysis 1993 VCH Weiheim
5. I. Ojima Catalytic Asymmetric Synthesis 1993 VCH New York
6. H.B. Kagan Comprehensive Organic Chemistry 8 1992 Pergamon Oxford
7. B. Bosnic Asymmetric Catalysis 1986 Martinus Nijhoff Dordrecht
8. K. Soai, and S. Niwa Chem. Rev. 92 1992 833
9. R. Noyori, and M. Kitamura Angew. Chem. 103 1991 34
10. R. Noyori, and M. Kitamura Angew. Chem. Int. Ed. Engl. 30 1991 49
11. N. Oguni, and T. Omi Tetrahedron Lett. 25 1984 2823
12. C. Bolm, K. Muniz, and J.P. Hildebrand Org. Lett. 1 1999 491
13. M. Kitamura, H. Oka, and R. Noyori Tetrahedron 55 1999 3605
14. P.I. Dosa, and G.C. Fu J. Am. Chem. Soc. 120 1998 445
15. P. ten Holte, J.-P. Wijgergangs, L. Thijs, and B. Zwanenburg Org. Lett. 1 1999 1095
16. M.I. Burguete, E. Garcia-Verdugo, M.J. Vicent, S.V. Luis, H. Pennemann, and N. Graf von Keyserling J. Martens, Org. Lett. 4 2002 3947
17. L. Sola, K.S. Reddy, A. Vidal-Ferran, A. Moyano, M.A. Pericas, A. Riera, A. Alvarez-Larena, and J.F. Piniella J. Org. Chem. 63 1998 7078
18. Y.-J. Cherng, J.-M. Fang, and T.-J. Lu J. Org. Chem. 64 1999 3207
19. M.R. Paleo, I. Cabeza, and F.J. Sardina J. Org. Chem. 65 2000 2108
20. J.M. Fraile, J.A. Mayoral, J. Serrano, M.A. Pericas, L. Sola, and D. Castellnou Org. Lett. 5 2003 4333
21. W.A. Nugent Org. Lett. 4 2002 2133
22. K.-H. Wu, and H.-M. Gau Organometallics 22 2003 5193
23. S. Degni, C.-E. Wilén, and R. Leino Tetrahedron: Asymmetr. 15 2004 231
24. M. Shi, Y. Satoh, T. Makihara, and Y. Masaki Tetrahedron: Asymmetr. 6 1995 2109
25. D. Steiner, S.G. Sethofer, C.T. Goralski, and B. Singaram Tetrahedron: Asymmetr. 13 2002 1477
26. R.D. Ionescu, A. Blom, and T. Frejd Tetrahedron: Asymmetr. 14 2003 2369
27. T. Ohga, S. Umeda, and Y. Kawanami Tetrahedron 57 2001 4825
28. C.A. de Parrodi, E. Juaristi, L. Quintero-Cortés, and P. Amador Tetrahedron: Asymmetr. 7 1996 1915
29. S. Malfait, L. Pélinski, and J. Brocard Tetrahedron: Asymmetr. 9 1998 2595
30. A.L. Braga, F. Vargas, C.C. Silveira, and L.H. de Andrade Tetrahedron Lett. 43 2002 2335
31. S. Bastin, N. Delebecque, F. Agbossou, J. Brocard, and L. Pélinski Tetrahedron: Asymmetr. 10 1999 1647
32. Q. Xu, H. Wang, X. Pan, A.S.C. Chan, and T.-K. Yang Tetrahedron Lett. 42 2001 6171
33. D. Tanner, H.T. Kornø, D. Guijarro, and P.G. Andersson Tetrahedron 54 1998 14213
34. I. Iovel, G. Oehme, and E. Lukevics Appl. Organomet. Chem. 12 1998 469
35. G. Palmieri Eur. J. Org. Chem. 4 1999 805
36. Q. Xu, G. Zhu, X. Pan, and A.S.C. Chan Chirality 4 2002 716
37. Q. Xu, X. Wu, X. Pan, A.S.C. Chan, and T.-K. Yang Chirality 14 2002 28
38. P.C.B. Page, S.M. Allin, S.J. Maddocks, and M.R.J. Elsegood J. Chem. Soc., Perkin Trans. 1 24 2002 2827
39. I. Sato, T. Saito, and K. Soai Chem. Commun. 24 2000 2471
40. M. Min Shi, Y. Satoh, and Y. Masaki J. Chem. Soc., Perkin Trans. 1 16 1998 2547
41. S. Abramson, M. Laspéras, A. Galarneau, D. Desplantier-Giscard, and D. Brunel Chem. Commun. 18 2000 1773
42. X.-W. Yang, J.-H. Sheng, C.-S. Da, H.-S. Wang, W. Su, R. Wang, and A.S.C. Chan J. Org. Chem. 65 2000 295
43. D.-H. Ko, K.H. Kim, and D.-C. Ha Org. Lett. 4 2002 3759
44. S.-W. Kang, D.-H. Ko, K.H. Kim, and D.-C. Ha Org. Lett. 5 2003 4517
45. H Wan, Y. Hu, Y. Liang, S. Gao, J. Wang, Z. Zheng, and X. Hu J. Org. Chem. 68 2003 8277
46. D.-X. Liu, L.-C. Zhang, Q. Wang, C.-S. Da, Z.-Q. Xin, R. Wang, M.C.K. Choi, and A.S.C. Chan Org. Lett. 3 2001 2733
47. S. Vyskocil, S. Jaracz, M. Smrcina, M. Sticha, V. Hanus, M. Polasek, and P. Kocovsky J. Org. Chem. 63 1998 7727
48. G. Bringmann, and M. Breuning Tetrahedron: Asymmetr. 9 1998 667
49. X. Shen, H. Guo, and K. Ding Tetrahedron: Asymmetr. 11 2000 4321
50. C. Dong, J. Zhang, W. Zheng, L. Zhang, Z. Yu, M.C.K. Choi, and A.S.C. Chan Tetrahedron: Asymmetr. 11 2000 2449
51. K. Ding, A. Ishii, and K. Mikami Angew. Chem. Int. Ed. 38 1999 497
52. H. Kodama, J. Ito, A. Nagaki, T. Ohta, and I. Furukawa Appl. Organomet. Chem. 14 2000 709
53. M. Shi, and W.-S. Sui Chirality 12 2000 574
54. Y.-X. Chen, L.-W. Yang, Y.-M. Li, Z.-Y. Zhou, K.-H. Lam, A.S.C. Chan, and H.-L. Kwong Chirality 12 2000 510
55. K. Mikami, R. Angelaud, K. Ding, A. Ishii, A. Tanaka, N. Sawada, K. Kudo, and M. Senda Chem. Eur. J. 7 2001 730
56. E.F. DiMauro, and M.C. Kozlowski Org. Lett. 3 2001 3053
57. U.K. Anyanwu, and D. Venkataraman Tetrahedron Lett. 44 2003 6445
58. T.I. Danilova, V.I. Rozenberg, Z.A. Starikova, and S. Bräse Tetrahedron: Asymmetr. 15 2004 223
59. D. Seebach, R. Dahinden, R.E. Marti, A.K. Beck, D.A. Plattner, and F.N.M. Kühnle J. Org. Chem. 60 1995 1788
60. K.V. Gothelf, and K.A. Jørgensen J. Org. Chem. 60 1995 6847
61. K.V. Gothelf, I. Thomsen, and K.A. Jørgensen J. Am. Chem. Soc. 118 1996 59
62. K.B. Jensen, K.V. Gothelf, R.G. Hazell, and K.A. Jørgensen J. Org. Chem. 62 1997 2471
63. B. Altava, M.I. Burguete, B. Escuder, S.V. Luis, and R.V. Salvador J. Org. Chem. 62 1997 3126
64. M.-Y. Shao, and H.-M. Gau Organometallics 17 1998 4822
65. D. Seebach, A. Pichota, A.K. Beck, A.B. Pinkerton, T. Litz, J. Karjalainen, and V. Gramlich Org. Lett. 1 1999 55
66. A.B. Charette, C. Molinaro, and C. Brochu J. Am. Chem. Soc. 123 2001 12168
67. P.Q. Nguyen, and H.J. Schäfer Org. Lett. 3 2001 2993
68. W. Adam, P.L. Alsters, R. Neumann, C.R. Saha-Möller, D. Seebach, and R. Zhang Org. Lett. 5 2003 725
69. C. Bolm, M. Zehnder, and D. Bur Angew. Chem. 102 1990 206
70. H. Huang, Z. Zheng, H. Chen, C. Bai, and J. Wang Tetrahedron: Asymmetr. 14 2003 1285
71. H. Huang, H. Chen, X. Hu, C. Bai, and Z. Zheng Tetrahedron: Asymmetr. 14 2003 297
72. H.-L. Kwong, and W.-S. Lee Tetrahedron: Asymmetr. 10 1999 3791
73. J. Kang, H.Y. Kim, and J.H. Kim Tetrahedron: Asymmetr. 10 1999 2523
74. Y.-W. Zhong, C.-S. Jiang, M.-H. Xu, and G.-Q. Lin Tetrahedron 60 2004 8861
75. H.J. Zhu, B.T. Zhao, G.Y. Zuo, C.U. Pittman Jr., W.M. Daic, and X.J. Haob Tetrahedron: Asymmetr. 12 2001 2613
76. Q. Xu, X. Wu, X. Pan, A.S.C. Chan, and T.-K. Yang Chirality 14 2002 28
77. H.C. Brown, G.-M. Chen, and P.V. Ramachandran Chirality 9 1997 506
78. F. Rahm, A. Fischer, and C. Moberg Eur. J. Org. Chem. 21 2003 4205
79. H. Zhang, and K.S. Chan J. Chem. Soc., Perkin Trans. 1 4 1999 381
80. D. Cunningham, E.T. Gallagher, D.H. Grayson, P.J. McArdle, C.B. Storey, and D.J. Wilcock J. Chem. Soc., Perkin Trans. 1 23 2002 2692
81. T. Rosner, P.J. Sears, W.A. Nugent, and D.G. Blackmond Org. Lett. 2 2000 2511
82. J. Va'zquez, M.A. Perica's, F. Maseras, and A. Lledo's J. Org. Chem. 65 2000 7303
83. S. Kitamura, H. Oka, and R. Noyori Tetrahedron 55 1999 3605
84. M. Yamakawa, and R. Noyori J. Am. Chem. Soc. 117 1995 6327
85. Y.-J. Chen, R.-X. Lin, and C. Chen Tetrahedron: Asymmetr. 15 2004 3561
86. E.D. Mihelich, and D.J. Eickhoff J. Org. Chem. 48 1983 4135
87. L.C. King J. Am. Chem. Soc. 66 1944 894
88. C. Chen, K. Tagami, and Y. Kishi J. Org. Chem. 60 1995 5386
89. K. Soai, A. Ookawa, T. Kaba, and K. Ogawa J. Am. Chem. Soc. 109 1987 7111
90. S.-W. Kang, D.-H. Ko, K.H. Kim, and D.-C. Ha Org. Lett. 5 2003 4517
91. Š. Vyskočil, S. Jaracz, M. Smrčina, M. Štícha, V. Hanuš, M. Polášek, and P. Koovský J. Org. Chem. 63 1998 7727
92. M. Kitamura, S. Suga, K. Kawai, and R. Noyori J. Am. Chem. Soc. 108 1986 6071