Progress of Chiral Bis(oxazoline)-Metal Complexes Utilized in Asymmetric Cyclopropanation

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QIAO Zhen, BIAN Qing-Hua, HOU Shi-Cong, WANG Min. Progress of Chiral Bis(oxazoline)-Metal Complexes Utilized in Asymmetric Cyclopropanation[J]. Chinese Journal of Organic Chemistry, 2004, 24(1): 15-22.

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1 Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919.
2 Singh, V. K.; DattaGupta, A.; Sekar, G. Synthesis 1997, 137.
3 Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1966, 7, 5239.
4 Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1975, 16, 1707.
5 Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1977, 18, 2599.
6 Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1982, 23, 685.
7 Aratani, T. Pure Appl. Chem. 1985, 57,1839.
8 Fritschi, H.; Leuteneggar, U.; Pfaltz, A. Angew. Chem., Int.Ed. Engl. 1986, 25, 1005.
9 Fritschi, H.; Leuteneggar, U.; Siegmann, K.; Pfaltz, A.; Keller,W.; Kratky, C. Helv. Chim. Acta 1988, 71,1541.
10 Fritschi, H.; Leuteneggar, U.; Pfaltz, A. Helv. Chim. Acta 1988, 71, 1553.
11 Muller, D.; Umbricht, G.; Fahrni, C.; Matt, P.; Pfaltz, A. Tetrahedron 1991, 74, 232.
12 Leutenegger, U.; Umbricht, G.; Fahrni, C.; Matt, P.; Ptaltz, A. Tetrahedron 1992, 48, 2143.
13 Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
14 Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem.Soc. 1991, 113, 726.
15 (a) Xu, M. H.; Lin, G. Q. Chin. J. Org. Chem. 2000, 20, 475 ( in Chinese ).
(徐明华, 林国强, 有机化学,2000, 20, 475.)
(b) Yao, X. Q.; Chen, H. L.; Zheng, Z. Prog. Chem. 2000, 12, 282 (in Chinese).
(姚小泉, 陈惠麟, 郑卓, 化学进展, 2000, 12, 282.)
(c) Xu, Y.; You, T. B.; Wang, Z. Y. Chem. Reag. 1999, 21, 347 (in Chinese).
(许毓, 尤田耙, 王忠义, 化学试剂, 1999, 21, 347.)
(d) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
(e) Tye, H. J. Chem. Soc., Perkin Trans. 1 2000, 275.
16 Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry1998, 9, 1.
17 Gao, M. Z.; Wang, B.; Xu, Z. L. Prog. Chem. 2002, 14(5), 347 (in Chinese).
(高明章, 汪波, 许遵乐, 化学进展, 2002, 14, 347.)
18 Lowenthal, R. E.; Masamune, J. Tetrahedron Lett. 1991,32, 7373.
19 Evans, D. A.; Woerpel, K. A.; Scott, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31(4), 430.
20 Evans, D. A.; Peterson, G. S.; Johnson, J. S.; Barnes, D. M.; Campos, K. R.; Woerpel, K. A. J. Org. Chem. 1998, 63, 4541.
21 Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
22 Matt, P.; Lioyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A. Helv. Chim. Acta 1995, 78, 265.
23 Pique, G.; Fahndrich, B.; Pfaltz, A. Synlett 1995, 491.
24 Ebinger, A.; Heinz, T.; Umbricht, G.; Pfaltz, A. Tetrahedron 1998, 54, 10469.
25 Temme, O.; Taj, S. A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007.
26 Schumacher, R.; Reissig, H. U. Synlett 1996,1121.
27 Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. J. Mol. Catal. A: Chem. 1999, 144, 85.
28 Fraile, J. M.; Garcia, J. I.; Herrias, C. I.; Mayorl, J. A.; Carrie, D.; Valtier, M. Tetrahedron: Asymmetry 2001, 12, 1891.
29 Ostergaard, N.; Jensen, J. F.; Tanner, D. Tetrahedron 2001, 57, 6083.
30 Thorhauge, J.; Roberson, M.; Hazell, R. G.; Anker, K.; Jorgensen, A. Chem. Eur. J. 2002, 8, 1888.
31 Koskinen, A. M. P.; Hassila, H. J. Org. Chem. 1993, 58, 4479.
32 Tokunoh, R.; Tomiyama, H.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 2449.
33 Denmark, S. E.; Stavenger, R. A.; Faucher, A. M.; Edwards, J. P. J.Org. Chem. 1997, 62, 3375.
34 Hoarau, O.; Ait-Haddou, H.; Castro, M.; Balavoine, G. G. A. Tetrahedron: Asymmetry 1997, 8, 3755.
35 Alexander, K.; Cook, S.; Gibson, C. L. Tetrahedron Lett. 2000, 41, 7135.
36 Clariana, J.; Comelles, J.; Moreno-Manas, M.; Vallribera, A. Tetrahedron: Asymmetry 2002, 13, 1551.
37 (a) Harm, A. M.; Knight, J. G.; Stemp, G. Synlett 1996, 677.
(b) Harm, A. M.; Knight, J. G.; Stemp, G. Tetrahedron Lett.1996, 37, 6189.
38 Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1996,37, 4073.
39 Bedekar, A. V.; Koroleva, E. B.; Andersson, P. G. J. Org. Chem. 1997, 62, 2518.
40 Denmark, S. E.; Nakajima, N.; Nicaise, O. J. C.; Faucher, A. M.; Edwards, J. P. J. Org. Chem. 1995, 60, 4884.
41 Boulch, R.; Scheurer, A.; Mosset, P.; Saalfrank, R. W. Tetrahedron Lett. 2000, 41, 1023.
42 DattaGupta, A.; Bhuniya, D.; Singh, V. K. Tetrahedron 1994, 50, 13725.
43 DattaGupta, A.; Singh, V. K. Tetrahedron Lett. 1996, 37, 2633.
44 Nishigama, H.; Itoh, Y.; Matsumoto, H.; Park, S. B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
45 Park, S. B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Asymmetry 1995, 6, 2489.
46 Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247.
47 Nishiyama, H.; Aoki, K.; Itoh, H.; Iwamura, T.; Sakata, N.; Kurihara, O.; Motoyuma, Y. Chem. Lett. 1996, 1071.
48 Nishiyama, H.; Soeka, N.; Naito, T.; Notoyama, Y. Tetrahedron: Asymmetry 1998, 9, 2865.
49 Wu, X. Y.; Shen, Y. Y.; Ma, B.; Zhou, Q. L.; Chan, A. S. C. J. Mol. Catal. A: Chem. 2000, 157, 59.
50 Chelucci, G.; Sanna, M. G.; Gladiali, S. Tetrahedron 2000, 56, 2889.
51 Gant, T. G.; Noe, M.C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745.
52 Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1997, 38, 2681.
53 Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Org. Chem. 2000, 65, 3326.
54 Uozumi, Y.; Kyota, H.; Kishi, E.; Kitayama, K.; Hayashi, T. Tetrahedron: Asymmetry 1996, 7, 1603.
55 Imai, Y.; Matsuo, S.; Zhang, W.; Nakatsuji, Y.; Ikeda, I. Synlett2000, 239.
56 Kim, S. G.; Cho, C. W.; Ahn, K. H. Tetrahedron: Asymmetry 1997, 8, 1023.
57 Kim, S. G.; Cho, C. W.; Ahn, K. H. Tetrahedron 1999, 55, 10079.
58 Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637.
59 Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron:Asymmetry 1997, 8, 2089.
60 Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Tarnai, T. Tetrahedron:Asymmetry 1998, 9, 3997.
61 Alonso, P. J.; Fraile, J. M.; Garcia, J.; Garcia, J. I.; Martinez, J. I.; Mayoral, J. A.; Sanchez, M.C. Langmuir 2000, 16, 5607.
62 Fernandez, M. J.; Fraile, J. M.; Garcia, J. I.; Mayoral, J. A.; Burguete, M. I.; Garcia-Verdugo, E.; Luis, S. V.; Harmer, M. A. Top. Catal. 2000, 13, 303.
63 Burguete, M. I.; Fraile, J. M.; Garcia, J. I.; Garcia-Verdugo, E.; Luis, S. V.; Mayoral, J. A. Org. Lett. 2000, 2, 3905.
64 Burgete, M. I.; Diez-Barra, E.; Fraile, J. M.; Garcia, J. I.; Garcia-Verdugo, E.; Gonzalez, R.; Herrerias, C. I.; Luis, S. V.; Mayoral, J. Bioorg.Med. Chem. 2002, 12, 1821.
65 Burgete, M. I.; Fraile, J. M.; Garcia, J. I.; Garcia-Verdugo, E.; Herrecias, C. I.; Luis, S. V.; Mayoral, J. A. J. Org. Chem. 2001, 66, 8893.
66 Clarke, R. J.; Shannon, I. J. Chem. Commun. 2001, 1936.
67 Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045.
68 Buckmann, A. F.; Morr, M. Makromol. Chem. 1981, 182, 1379.
69 Mutter, M.; Altmann, R. H.; Gehrhardt, H. React. Polym.1987, 6, 99.
70 Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Pitillo, M. J. Org. Chem. 2001, 66, 3160.

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