Enantioselective silylcyanation of aldehydes catalyzed by new chiral oxovanadium complex

Tetrahedron Asymmetry

Volumn 22, Issue 23, 2011, Pages 1981-1984

  Chu, Chang Ying ^a   Hsu, Chu Tin ^a   Lo, Po Hsiang ^a   Uang, Biing Jiun ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CYANOHYDRIN; METAL COMPLEX; OXOVANADIUM COMPLEX; SALICYLALDEHYDE; SCHIFF BASE; UNCLASSIFIED DRUG; VALINE; VANADIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYANATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SILYLATION;

EID: 84856110853     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.11.007     Document Type: Article

References (93)

1. M. North Synlett 1993 807
2. F. Effenberger Angew. Chem., Int. Ed. Engl. 33 1994 1555
3. H. Griengl, A. Hickel, D.V. Johnson, C. Krathy, M. Schmidt, and H. Schwab Chem. Commun. 1997 1933
4. R.J.H. Gregory Chem. Rev. 99 1999 3649
5. S. Norsikian, I. Holmes, F. Lagasse, and H.B. Kagan Tetrahedron Lett. 43 2002 5715
6. M. North Tetrahedron: Asymmetry 14 2003 147
7. J.-M. Brunel, and I.P. Holmes Angew. Chem., Int. Ed. 43 2004 2752
8. Y.N. Belokon, M. North, V.I. Maleev, N.V. Voskoboev, M.A. Moskalenko, A.S. Peregudov, A.V. Dmitriev, N.S. Ikonnikov, and H.B. Kagan Angew. Chem., Int. Ed. 43 2004 4085
9. F.-X. Chen, and X. Feng Synlett 2005 892
10. M. North, D.L. Usanov, and C. Young Chem. Rev. 108 2008 5146
11. I. Ojima Catalytic Asymmetric Synthesis 2000 Wiley New York
12. (b) A. Mori, and S. Inoue Cyanation of Carbonyl and Amino Groups E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Synthesis 1999 Springer Heidelberg
13. J.A. Vale, W.M. Faustino, P.H. Menezes, and G.F. De Sa Chem. Commun. 2006 3340
14. Y.N. Belokon, V.I. Maleev, I.L. Malfanov, T.F. Saveleva, N.S. Ikonnikov, A.G. Bulychev, D.L. Usanov, D.A. Kataev, and M. North Russ. Chem. Bull. 55 2006 821
15. J. Casas, C. Nájera, J.M. Sansano, and J.M. Saá Org. Lett. 4 2002 2589
16. T. Ziegler, B. Horsch, and F. Effenberger Synthesis 1990 575
17. F. Effenberger, T. Ziegler, and S. Forster Angew. Chem., Int. Ed. Engl. 26 1987 458
18. P. Zandbergaen, J. Van der Linden, J. Brussee, and A. van der Gen Synth. Commun. 21 1991 1387
19. J. Brussee, E.C. Roos, and A. van der Gen Tetrahedron Lett. 29 1988 4485
20. V.J. Ognyanov, V.K. Datcheva, and K.S. Kyler J. Am. Chem. Soc. 113 1991 6992
21. Y. Lu, C. Miet, N. Kunesch, and J.E. Poisson Tetrahedron: Asymmetry 4 1993 893
22. M. Hayashi, T. Matsuda, and N. Oguni J. Chem. Soc., Chem. Commun. 1990 1364
23. A. Mori, H. Ohno, H. Nitta, K. Tanaka, and S. Inoue Synlett 1991 563
24. H. Nitta, D. Yu, M. Kudo, A. Mori, and S. Inoue J. Am. Chem. Soc. 114 1992 7969
25. M. Hayashi, T. Matsuda, and N. Oguni J. Chem. Soc., Perkin Trans. 1 58 1992 3135
26. M. Hayashi, Y. Miyamoto, T. Inoue, and N. Oguni J. Org. Chem. 58 1993 1515
27. C. Bolm, and P. Muller Tetrahedron Lett. 36 1995 1625
28. W.D. Pan, X.M. Feng, L.Z. Gong, W.H. Hu, Z. Lin, and Y.Z. Jiang Synlett 1996 337
29. I. Iovel, Y. Popelis, M. Fleisher, and E. Vukevics Tetrahedron: Asymmetry 8 1997 1279
30. M. Wada, T. Takahashi, T. Domae, T. Fukuma, N. Miyoshi, and K. Smith Tetrahedron: Asymmetry 8 1997 3939
31. Y.N. Belekon, and M. North J. Am. Chem. Soc. 121 1999 3968
32. J.-S. You, H.-M. Gau, and M.C.K. Choi Chem. Commun. 2000 1963
33. T. Ooi, T. Miura, K. Takaya, H. Ichikawa, and K. Maruoka Tetrahedron 57 2001 867
34. Y.N. Belekon, A.V. Gutnov, M.A. Moscalenko, L.V. Yashkina, D.E. Lesovoy, N.S. Ikonnikov, V.S. Larichev, and M. North Chem. Commun. 2002 244
35. S. Liang, and X.R. Bu J. Org. Chem. 67 2002 2702
36. W. Hwang, Y. Song, C. Bai, G. Cao, and Z. Zheng Tetrahedron Lett. 45 2004 4763
37. Y. Li, B. He, B. Qin, X. Feng, and G. Zhang J. Org. Chem. 69 2004 7910
38. S. Lundgren, E. Wingstrand, M. Penhoat, and C. Moberg J. Am. Chem. Soc. 127 2005 11592
39. Z.-B. Li, A.R. Rajaram, N. Decharin, Y.-C. Qin, and L. Pu Tetrahedron Lett. 46 2005 2223
40. Y.N. Belokon, A.J. Blacker, L.A. Clutterbuck, D. Hogg, M. North, and C. Reeve Eur. J. Org. Chem. 2006 4609
41. A. Hamber, S. Lundgren, M. Penhoat, C. Moberg, and K. Hult J. Am. Chem. Soc. 128 2006 2234
42. S.-K. Chen, D. Peng, H. Zhou, L.-W. Wang, F.-X. Chen, and X.M. Feng Eur. J. Org. Chem. 2007 639
43. Z. Zeng, G. Zhao, P. Gao, H. Tang, B. Chen, Z. Zhou, and C. Tang Catal. Commun. 8 2007 1443
44. E.J. Corey, and Z. Wang Tetrahedron Lett. 34 1993 4001
45. T. Ooi, K. Takaya, T. Miura, H. Ichikawa, and K. Maruoka Synlett 2000 1133
46. H. Ohno, H. Nitta, K. Tanaka, A. Mori, and S. Inoue J. Org. Chem. 57 1992 6778
47. Y. Hamashima, D. Sawada, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 121 1999 2641
48. Y. Hamashima, D. Sawada, H. Nogami, M. Kanai, and M. Shibasaki Tetrahedron 57 2001 805
49. M. Kanai, Y. Hamashima, and M. Shibasaki Tetrahedron Lett. 41 2000 2405
50. H. Gröger Chem. Eur. J. 7 2001 5247
51. J. Casas, A. Baeza, J.M. Sansano, C. Nájera, and J.M. Saá Tetrahedron: Asymmetry 14 2003 197
52. S.S. Kim, and D.H. Song Eur. J. Org. Chem. 2005 1777
53. S. Gou, J. Wang, X. Liu, W. Wang, F.-X. Chen, and X. Feng Adv. Synth. Catal. 349 2007 343
54. A. Baeza, C. Nájera, J.M. Sansano, and J.M. Saá Pure Appl. Chem. 79 2007 213
55. A. Abiko, and G.-Q. Wang J. Org. Chem. 61 1996 2264
56. A. Abiko, and G.-Q. Wang Tetrahedron 54 1998 11405
57. J. Tian, N. Yamagiwa, S. Matsunaga, and M. Shibasak Angew. Chem., Int. Ed. 41 2002 3636
58. N. Yamagiwa, J. Tian, S. Matsunaga, and M. Shibasaki J. Am. Chem. Soc. 27 2005 3413
59. C. Qian, C. Zhu, and T. Huang J. Chem. Soc., Perkin Trans. 1 1998 2131
60. H.C. Aspinall, N. Greeves, and P.M. Smith Tetrahedron Lett. 40 1999 1763
61. W.-B. Yang, and J.-M. Fang J. Org. Chem. 63 1998 1356
62. K. Yabu, S. Masumoto, Y. Yamasaki, Y. Hamashima, M. Kanai, W. Du, D.P. Curran, and M. Shibasaki J. Am. Chem. Soc. 123 2001 9908
63. M. Suzuki, N. Kato, K. Kanai, and M. Shibasaki Org. Lett. 7 2005 2527
64. K. Maki, R. Motoki, K. Fujii, M. Kanai, T. Kobayashi, S. Tamura, and M. Shibasaki J. Am. Chem. Soc. 127 2005 17111
65. S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama Chem. Lett. 1991 541
66. Y.N. Belekon, M. North, and T. Parsons Org. Lett. 2 2000 1617
67. Y.N. Belekon, B. Green, N.S. Ikonnikov, M. North, V. Parsons, and V.I. Tararov Tetrahedron 57 2001 771
68. Y. Sakai, J. Mitote, K. Matsumoto, and T. Katsuki Chem. Commun. 46 2010 5787
69. A. Watanabe, K. Matsumoto, Y. Shimada, and T. Katsuki Tetrahedron Lett. 45 2004 6229
70. S. Hanessian, G.J. Reddy, and N. Chahal Org. Lett. 8 2006 5477
71. Y.N. Belokon, V.I. Maleev, M. North, and D.L. Usanov Chem. Commun. 2006 4614
72. Y.N. Belekon, W. Clegg, R.W. Harrington, M. North, and C. Young Inorg. Chem. 47 2008 3801
73. C.-D. Hwang, D.-R. Hwang, and B.-J. Uang J. Org. Chem. 63 1998 6762
74. C.-W. Chang, C.-T. Yang, C.-D. Hwang, and B.-J. Uang Chem. Commun. 2002 54
75. B.-J. Uang, I.-P. Fu, C.-D. Hwang, C.-W. Chang, C.-T. Yang, and D.-R. Hwang Tetrahedron 60 2004 10479
76. C.-Y. Chu, D.-R. Hwang, S.-K. Wang, and B.-J. Uang Chem. Commun. 2001 980
77. C.-Y. Chu, and B.-J. Uang Tetrahedron: Asymmetry 14 2003 53
78. L.J. Theriot, G.O. Carlisle, and H.J. Hu J. Inorg. Nucl. Chem. 31 1969 2841
79. J.J.R. Frausto da Silva, R. Wootton, and R.D. Gillard J. Chem. Soc. A. 1970 3369
80. I. Cavado, J.C. Pessoa, D. Costa, M.T. Duarte, R.D. Gillard, and P. Matias J. Chem. Soc., Dalton. Trans. 1994 149
81. R. Fulwood, H. Schmidt, and D. Rehder J. Chem. Soc., Chem. Commun. 1995 1443
82. W. Chen, S. Gao, and S.-X. Liu Acta Crystallogr., Sect. C 55 1999 531
83. C. Grüning, H. Schmidt, and D. Rehder Inorg. Chem. Commun. 2 1999 57
84. R. Hämäläinen, U. Turpeinen, and M. Ahlgrn Acta Crystallogr, Sect. C 41 1985 1726
85. K. Nakajima, M. Kojima, K. Toriumi, K. Saito, and J. Fujita Bull. Chem. Soc. Jpn. 62 1989 760
86. V. Vergopoulos, W. Priebsch, M. Fritzsche, and D. Rehder Inorg. Chem. 32 1993 1844
87. I. Cavaco, J.C. Pessoa, M.T. Duarte, R.D. Gillard, and P. Matias Chem. Commun. 1996 1365
88. I. Cavaco, J.C. Pessoa, M.T. Duarte, R.T. Henriques, P.M. Matias, and R.D. Gillard J. Chem. Soc., Dalton Trans. 1996 1989
89. K.K. Rajak, S.P. Rath, S. Mondal, and A. Chakravorty Inorg. Chem. 38 1999 3283
90. J.C. Pessoa, M.J. Calhorda, I. Cavaco, I. Correia, M.T. Duarte, V. Felix, R.T. Henriques, M.F.M. Piedade, and I. Tomaz J. Chem. Soc., Dalton Trans. 2002 4407
91. E.D. Soli, A.S. Manoso, M.C. Patterson, and P. DeShong J. Org. Chem. 64 1999 3171
92. M.G. Dekamin, and Z. Karimi J. Organomet. Chem. 694 2009 1789
93. M.G. Dekamin, S. Sagheb-Asl, and M.R. Naimi-Jamal Tetrahedron Lett. 50 2009 4063