Storable and air-stable zirconium complex-catalyzed highly enantioselective darzens reaction of diazoacetamide with aldehydes

Advanced Synthesis and Catalysis

Volumn 352, Issue 7, 2010, Pages 1123-1127

  He, Long ^a   Liu, Wei Jun ^a   Ren, Lei ^a   Lei, Tao ^a   Gong, Liu Zhu ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Asymmetric catalysis; Cis glycidic amides; Darzens reaction; Epoxides; Zirconium lewis acids

Indexed keywords

EID: 77952167037     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.200900845     Document Type: Article

References (53)

1. For review, see a) Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su, Chem. Rev. 2005, 105, 1603-1662;
2. b) A.H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341-2372;
3. c) O. A. Wong, Y. Shi, Chem. Rev. 2008, 108, 3958-3987;
4. d) B. S. Lane, K. Burgess, Chem. Rev. 2003, 103, 2457-2473.
5. a) E. N. Jacobsen, L. Deng, Y. Furukawa, L. E. Martinez, Tetrahedron 1994, 50, 4323-4334;
6. b) J. R. Flisak, K. J. Gombatz, M. M. Holmes, A. A. Jarmas, I. Lantos, W. L. Mendelson, V. J. Novack, J. J. Remich, L. Snyder, J. Org. Chem. 1993, 58, 6247-6254;
7. c) A. V. R. Rao, S. P. Rao, M. N. Bhanu, J. Chem. Soc. Chem. Commun. 1992, 859-860.
8. a) R. A. Johnson, K. B. Sharpless, in: Catalytic Asymmetric Synthesis, (Ed.: I. Ojima), VCH, New York, 1993, pp 227-272;
9. b) E. N. Jacobsen, in: Catalytic Asymmetric Synthesis, (Ed.: I. Ojima), VCH, New York, 1993, pp 159-202.
10. a) H. C. Kolb, M.S. Vannieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547;
11. b) C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald, P. J. Murray, Angew. Chem. 1997, 109, 379-381;
12. Angew. Chem. Int. Ed. Engl. 1997, 36, 410-412;
13. c) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329-2330;
14. d) S. Matsunaga, T. Kinoshita, S. Okada, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 7559-7570;
15. e) M. J. Porter, J. Skidmore, Chem. Commun. 2000, 1215-1225;
16. f) M. Wu, B. Wang, S.-F. Wang, C.-G. Xia, W. Sun, Org. Lett. 2009, 11, 3622-3625.
17. For a review, see: T. Rosen, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon, Oxford, 1991, Vol.2, p 409.
18. a) S. Arai, Y. Shirai, T. Ishida, T. Shioiri, Chem. Commun. 1999, 49-50;
19. b) S. Arai, K. Tokumaru, T. Aoyama, Tetrahedron Lett. 2004, 45, 1845-1848;
20. c) P. Bakó, K. Vizárdi, Z. Bajor, L. Tõke, Chem. Commun. 1998, 1193-1194;
21. d) T. J. R. Achard, Y. N. Belokon, M. Ilyin, M. Moskalenko, M. North, F. Pizzato, Tetrahedron Lett. 2007, 48, 2965-2969;
22. e) R. Imashiro, T. Yamanaka, M. Seki, Tetrahedron: Asymmetry 1999, 10, 2845-2851;
23. f) V. K. Aggarwal, G. Hynd, W Picoul, J. L. Vasse, J. Am. Chem. Soc. 2002, 124, 9964-9965;
24. g) V. K. Aggarwal, J. P. H. Charmant, D. Fuentes, J. N. Harvey, G. Hynd, D. Ohara, W. Picoul, R. Robiette, C. Smith, J. L. Vasse, C. L. Winn, J. Am. Chem. Soc. 2006, 128, 2105-2114.
25. W.-J. Liu, B.-D. Lv, L.-Z. Gong, Angew. Chem. 2009, 121, 6625-6628;
26. Angew. Chem. Int. Ed. 2009, 48, 6503-6506.
27. S. Kobayashi, M. Ueno, S. Saito, Y. Mizuki, H. Ishitami, Y. Yamashita, Proc. Natl. Acad. Sci. USA 2004, 101, 5476-5481.
28. a) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 1997, 119, 7153-7154;
29. b) S. Kobayashi, H. Ishitani, M. Ueno, J. Am. Chem. Soc. 1998, 120, 431-432;
30. c) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 8180-8186;
31. d) K. Saruhashi, S. Kobayashi, J. Am. Chem. Soc. 2006, 128, 11232-11235;
32. e) Y. Ihori, Y. Yamashita, H. Ishitani, S. Kobayashi, J. Am. Chem. Soc. 2005, 127, 15528-15535;
33. f) S. Xue, S. Yu, Y.-H. Deng, W. D. Wulff, Angew. Chem. 2001, 113, 2331-2334;
34. Angew. Chem. Int. Ed. 2001, 40, 2271-2274;
35. g) M. Ueno, H. Ishitani, S. Kobayashi, Org. Lett. 2002, 4, 3395-3397.
36. a) Y. Yamashita, H. Ishitani, H. Shimizu, S. Kobayashi, J. Am. Chem. Soc. 2002, 124, 3292-3302;
37. b) T. Isoda, R. Akiyama, H. Oyamada, S. Kobayashi, Adv. Synth. Catal. 2006, 348, 1813-1817;
38. c) S. Kobayashi, S. Saito, M. Ueno, Y. Yamashita, Chem. Commun. 2003, 2016-2017;
39. d)W.-G. Yao, J.-B. Wang, Org. Lett. 2003, 5, 1527-1530.
40. a) H. Ishitani, S. Komiyama, S. Kobayashi, Angew. Chem. 1998, 110, 3369-3372;
41. Angew. Chem. Int. Ed. 1998, 37, 3186-3188;
42. b) H. Ishitani, S. Komiyama, Y. Hasegawa, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 762-766.
43. a) S. Kobayashi, H. Shimizu, Y. Yamashita, H. Ishitani, J. Kobayashi, J. Am. Chem. Soc. 2002, 124, 13678-13679;
44. b) Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 11279-11282.
45. a) S. Kobayashi, S. Komiyama, H. Ishitani, Angew. Chem. 1998, 110, 1026-1028;
46. Angew. Chem. Int. Ed. 1998, 37, 979-981;
47. b) S. Kobayashi, K. Kusakabe, S. Komiyama, H. Ishitani, J. Org. Chem. 1999, 64, 4220-4221;
48. c) S. Kobayashi, K. Kusakabe, H. Ishitani, Org. Lett. 2000, 2, 1225-1227;
49. d) Y. Yamashita, S. Saito, H. Ishitani, S. Kobayashi, Org. Lett. 2002, 4, 1221-1223;
50. e) Y. Yamashita, S. Saito, H. Ishitani, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3793-3798.
51. T. Gastner, H. Ishitani, R. Akiyama, S. Kobayashi, Angew. Chem. 2001, 113, 1949-1951;
52. Angew. Chem. Int. Ed. 2001, 40, 1896-1898.
53. T. Okachi, N. Murai, M. Onaka, Org. Lett. 2003, 5, 85-87.