Versatile supramolecular copper(II) Complexes for Henry and Aza-Henry reactions

Advanced Synthesis and Catalysis

Volumn 351, Issue 9, 2009, Pages 1255-1262

  Zhang, Guoqi ^a   Yashima, Eiji ^b   Woggon, Wolf D ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

Aza henry reaction; Catalysis; Copper(II); Enantioselectivity; Henry reaction

Indexed keywords

EID: 67549146547     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900069     Document Type: Article

References (63)

1. J. Boruva, N Gogoi, P. P. Saikia, N. C. Barua, Tetrahedron: Asymmetry 2006, 17, 3315-3326.
2. a) N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001;
3. b) G. Rosini, in: Comprehensive Organic Synthesis, Vol. 2, (Eds. : B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon, New York, 1991, pp 321-340;
4. c) C. Palomo, M. Oiarbide, A. Laso, Eur. J. Org. Chem. 2007, 2561-2574.
5. a) T Ooi, K. Doda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 2054-2055;
6. b) T. R Yoon, E. N. Jacobsen, Angew. Chem. 2005, 117, 470-472;
7. Angew. Chem. Int. Ed. 2005, 44, 466-468;
8. c) H. Li, B. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 732-733.
9. a) H. Sasai, T Suzuki, S. Arai, T Arai, M. Shibasaki, J. Am. Chem. Soc. 1992, 114, 4418-4420;
10. b) M. Shibasaki, N Yoshikawa, Chem. Rev. 2002, 102, 2187-2210;
11. c) T. Purkarthofer, K. Gruber, M. Gruber-Khadjawi, K. Waich, W. Skranc, D. Mink, H. Griengl, Angew. Chem. 2006, 118, 3532-3535;
12. Angew. Chem. Int. Ed. 2006, 45, 3454-3456;
13. d) B. M. Trost, V. S. C. Yeh, Angew. Chem. 2002, 114, 889-891;
14. Angew. Chem. Int. Ed. 2002, 41, 861-863;
15. e) C. Palomo, M. Oiarbide, A. Laso, Angew. Chem. 2005, 117, 3949-3952;
16. Angew. Chem. Int. Ed. 2005, 44, 3881-3884;
17. f) D. A. Evans, D. Seidel, M. Rueping, H. W. Lam, J. T Shaw, C. W. Downey, J. Am. Chem. Soc. 2003, 125, 12692-12693;
18. g) K. Ma, J. You, Chem. Eur. J. 2007, 13, 1863-1871;
19. h) M. Bandini, F. Piccinelli, S. Tommasi, A. Umani-Ronchi, C. Ventrici, Chem. Commun. 2007, 616-618;
20. i) Y. Xiong, F. Wang, X. Huang, Y. Wen, X. Feng, Chem. Eur. J. 2007, 13, 829-833;
21. j) T. Arai, N. Yokoyama, A. Yanagisawa, Chem. Eur. J. 2008, 14, 2052-2059;
22. k) C. Gan, G. Lai, Z. Zhang, Z. Wang, M.-M. Zhou, Tetrahedron: Asymmetry 2006, 17, 725-728;
23. l) G. Blay, E. Climent, I. Fernandez, V. Hernandez-Olmos, J. R. Pedro, Tetrahedron: Asymmetry 2006, 17, 2046-2049;
24. m) G. Blay, L. R. Domingo, V. Hernandez-Olmos, J. R. Pedro, Chem. Eur. J. 2008, 14, 4725-4730;
25. n) Q. T Nguyen, J. H. Jeong, Polyhedron 2006, 25, 1787-1790.
26. a) K. Tanaka, S. Hachiken, Tetrahedron Lett. 2008, 49, 2533-2536;
27. b) T. Arai, M. Watanabe, A. Yanagisawa, Org. Lett. 2007, 9, 3595-3597;
28. c) S. K. Ginotra, V. K. Singh, Org. Biomol. Chem. 2007, 5, 3932-3937;
29. d) Q. T. Nguyen, J. H. Jeong, Polyhedron 2006, 25, 1787-1790;
30. e) T. Kato, K. Marubayashi, S. Takizawa, H. Sasai, Tetrahedron: Asymmetry 2004, 15, 3693-3697;
31. f) H. Zhou, D. Peng, B. Qin, Z. Hou, X. Liu, X. Feng, J. Org. Chem. 2007, 72, 10302-10304;
32. g) Y. Zhang, L. Xiang, Q. Wang, X.-F. Duan, G. Zi, Inorg. Chim. Acta 2008, 361, 1246-1254;
33. h) K. Ma, J. You, Chem. Eur. J. 2007, 13, 1863-1871;
34. i) A. Toussaint, A. Pfalz, Eur. J. Org. Chem. 2008, 4591-4597.
35. a) C.-T. Yeung, H.-L. Yeung, C.-S. Tsang, W.-Y. Wong, H.-L. Kwong, Chem. Commun. 2007, 5203-5205;
36. b) V. Amendola, L. Fabbrizzi, C. Mangano, P. Pallavicini, E. Roboli, M. Zema, Inorg. Chem. 2000, 39, 5803-5806;
37. c) M. Ziegler, A. Von Zelewsky, Coord. Chem. Rev. 1998, 177, 257-300;
38. d) W. Zarges, J. Hall, J.-M. Lehn, C. Bolm, Helv. Chim. Acta 1991, 74, 1843-1852.
39. a) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772;
40. Angew. Chem. Int. Ed. 1998, 37, 2580-2627.
41. a) H. W. Pinnick, Org. React. 1990, 38, 655-792;
42. b) R. Ballini, M. Petrini, Tetrahedron 2004, 60, 1017-1047;
43. c) E. Foresti, G. Palmieri, M. Petrini, R. Profeta, Org. Biomol. Chem. 2003, 1, 4275-4281.
44. For a pioneering work, see : K.-I. Yamada, S. J. Harwood, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 3713-3715;
45. Angew. Chem. Int. Ed. 1999, 38, 35043506.
46. For a review, see : B. Westermann, Angew. Chem. 2003, 115, 161-163;
47. Angew. Chem. Int. Ed. 2003, 42, 151-153.
48. For selected examples, see: a) T Okino, S. Nakamura, T Furukawa, Y. Takemoto, Org. Lett. 2004, 6, 625-627;
49. b) A. Lee, W. Kim, J. Lee, T. Hyeon, B. M. Kim, Tetrahedron: Asymmetry 2004, 15, 2595-2598;
50. c) F. Fini, V. Sgarzani, D. Pettersen, R. P. Herrera, L. Bernardi, A. Ricci, Angew. Chem. 2005, 117, 8189-8192;
51. Angew. Chem. Int. Ed. 2005, 44, 7975-7978;
52. d) L. Bernardi, F. Fini, R. P. Herrera, A. Ricci, V. Sgarzani, Tetrahedron 2006, 62, 375-380;
53. e) C. Palomo, M. Oiarbide, R. Halder, A. Laso, R. López, Angew. Chem. 2006, 118, 123-126;
54. Angew. Chem. Int. Ed. 2006, 45, 117-120;
55. f) F. Gao, J. Zhu, Y. Tang, M. Deng, C. Qian, Chirality 2006, 18, 741-745;
56. g) X. Xu, T. Furukawa, T. Okino, H. Miyabe, Y. Takemoto, Chem. Eur. J. 2006, 12, 466-476;
57. h) B. M. Nugent, R. A. Yoder, J. N Johnston, J. Am. Chem. Soc. 2004, 126, 3418-3419;
58. i) C. Palomo, M. Oiarbide, A. Laso, R. López, J. Am. Chem. Soc. 2005, 127, 17622-17623;
59. j) S. Handa, V. Gnanadesikan, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 4900-4901;
60. k) B. M. Trost, D. W. Lupton, Org. Lett. 2007, 9, 2023-2026;
61. l) H. Zhou, D. Peng, B. Qin, Z. Hou, X. Liu, X. Feng, J. Org. Chem. 2007, 72, 10302-10304;
62. m) C. Tan, X. Liu, L. Wang, J. Wang, X. Feng, Org. Lett. 2008, 10, 5305-5308.
63. For a non-enantioselective version of Henry reaction in aqueous media, see: R. Ballini, G. Bosica, J. Org. Chem. 1997, 62, 425-427.