Catalytic asymmetric Nozaki-Hiyama reactions with a tridentate bis(oxazolinyl)carbazole ligand

Chemical Record

Volumn 8, Issue 3, 2008, Pages 169-181

  Inoue, Masahiro ^a   Suzuki, Takahiro ^a   Kinoshita, Akihiro ^a   Nakada, Masahisa ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

Asymmetric catalysis; Ligand; Nozaki Hiyama reaction

Indexed keywords

EID: 53249107785     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.20148     Document Type: Article

References (71)

1. (a) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J Am Chem Soc 1977, 99, 3179;
2. (b) Okude, Y.; Hiyama, T.; Nozaki, H. Tetrahedron Lett 1977, 18, 3829.
3. Recent reviews: (a) Takai, K.; Nozaki, H. Proc Jpn Acad Ser B 2000, 76B(8), 123;
4. (b) Fürstner, A. Chem Rev 1999, 99, 991;
5. (c) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1, 1;
6. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jimenez, J. L.; Palacios, J. C. Chem Soc Rev 1999, 28, 169.
7. (a) Fürstner, A.; Shi, N. J Am Chem Soc 1996, 118, 12349;
8. (b) Fürstner, A.; Shi, N. J Am Chem Soc 1996, 118, 2533.
9. (a) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Morganti, S.; Umani-Ronchi, A. Org Lett 2001, 3, 1153;
10. (b) Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A. Pure Appl Chem 2001, 73, 325;
11. (c) Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron 2001, 57, 835;
12. (d) Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A. Polyhedron 2000, 19, 537;
13. (e) Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A. Angew Chem Int Ed 2000, 39, 2327;
14. (f) Bandini, M.; Cozzi, P. G.; Melchiorre, P.; Morganti, S.; Umani-Ronchi, A. Angew Chem Int Ed 1999, 38, 3357.
15. Asymmetric allylations not via a catalytic process: (a) Sugimoto, K.; Aoyagi, S.; Kibayashi, C. J Org Chem 1997, 62, 2322;
16. (b) Chen, C.; Tagami, K.; Kishi, Y. J Org Chem 1995, 60, 5386;
17. (c) Cazes, B.; Verniere, C.; Goré, J. Synth Commun 1983, 13, 73.
18. Inoue, M.; Suzuki, T.; Nakada, M. J Am Chem Soc 2003, 125, 1140.
19. Suzuki, T.; Kinoshita, A.; Kawada, H.; Nakada, M. Synlett 2003, 570.
20. Inoue, M.; Nakada, M. Org Lett 2004, 6, 2977.
21. Inoue, M.; Nakada, M. Heterocycles 2007, 72, 133.
22. (a) Cahiez, G.; Chavant, P. Y. Tetrahedron Lett 1989, 30, 7373;
23. (b) Hiyama, T.; Sawahata, M.; Obayashi, M. Chem Lett 1983, 1237.
24. (a) Le Doussal, B.; Le Coq, A.; Gorgues, A.; Meyer, A. Tetrahedron 1983, 39, 2185;
25. (b) Cazes, B.; Vernière, C.; Gorè, J. Tetrahedron Lett 1982, 23, 3501.
26. Ruck, R.; Jacobsen, E. N. J Am Chem Soc 2002, 124, 2882.
27. Inoue, M.; Nakada, M. Angew Chem Int Ed Engl 2006, 45, 252.
28. (a) Belyk, K.; Rozema, M. J.; Knochel, P. J Org Chem 1992, 57, 4070;
29. (b) Place, P.; Vernière, C.; Goré, J. Tetrahedron 1981, 37, 1359.
30. Brown, H. C.; Khire, U. R.; Narla, G. J Org Chem 1995, 60, 8130.
31. (a) Nakada, M.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett 1994, 35, 741;
32. (b) Johnson, W. S.; Chan, M. F. J Org Chem 1985, 50, 2598.
33. Inoue, M.; Nakada, M. J Am Chem Soc 2007, 129, 4164.
34. (a) Hatori, H.; Sato, B.; Sato, I.; Shibata, T.; Tsurumi, Y.; Sakamoto, K.; Takase, S.; Ueda, H.; Hino, M.; Fujii, T. J Antibiot 2004, 57, 264;
35. (b) Hatori, H.; Sato, B.; Sato, I.; Shibata, T.; Ueda, H.; Hino, M.; Fujii, T. J Antibiot 2004, 57, 390.
36. (a) Gaw, A.; Packard, C. J.; Shepherd, J. (Eds.) Statins: The HMG CoA Reductase Inhibitors in Perspective, 2nd ed.; Martin Dunitz: London, 2004;
37. (b) Tobert, J. A. Nat Rev Drug Discov 2003, 2, 517;
38. (c) Endo, A. J Lipid Res 1992, 33, 1569.
39. To the best of our knowledge, 13 and 14 are the first naturally occurring statins possessing a tetralin core. An early review: Rosen, T.; Heathcock, C. H. Tetrahedron 1986, 42, 4909.
40. Wu, X.; Nilsson, P.; Larhed, M. J Org Chem 2005, 70, 346.
41. Trnka, T. M.; Grubbs, R. H. Acc Chem Res 2001, 34, 18.
42. Crabtree, R. H.; Morris, G. E. J Organomet Chem 1977, 135, 395.
43. Nicolaou, K. C.; Daines, R. A.; Uenishi, J.; Li, W. S.; Papahatjis, D. P.; Chakraborty, T. K. J Am Chem Soc 1988, 110, 4672.
44. (a) Nagata, W.; Hayase, Y. J Chem Soc C 1969,460;
45. (b) Friese, A.; Hell-Momeni, K.; Zündorf, I.; Winckler, T.; Dingermann, T.; Dannhardt, G. J Med Chem 2002, 45, 1535.
46. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
47. For the precedent synthesis of the β-hydroxy-δ-lactone moiety, see: Ghosh, A. K.; Lei, H. J Org Chem 2000, 65, 4779.
48. Miyashita, M.; Suzuki, T.; Hoshino, M.; Yoshikoshi, A. Tetrahedron 1997, 53, 12469.
49. Recent reviews: (a) Daly, E. M.; Taylor, R. E. Chemtracts 2007, 20, 1;
50. (b) Hargaden, G. C.; Guiry, P. J Adv Syn Cat 2007, 349, 2407.
51. (a) Kim, H.-J.; Kishi, Y. J Am Chem Soc 2008, 130, 1842;
52. (b) Hargaden, G. C.; O'Sullivan, T. P.; Guiry, P. J Org Biomol Chem 2008, 6, 562;
53. (c) Hargaden, G. C.; MJller-Bunz, H.; Guiry, P. J. Eur J Org Chem 2007, 4235;
54. (d) Hargaden, G. C.; McManus, H. A.; Cozzi, P. G.; Guiry, P. J Org Biomol Chem 2007, 5, 763;
55. (e) Xia, G.; Yamamoto, H. J Am Chem Soc 2007, 129, 496;
56. (f) Miller, J. J.; Sigman, M. S. J Am Chem Soc 2007, 129, 2752;
57. (g) Smith, K. M. Coord Chem Rev 2006, 250, 1023;
58. (h) McManus, H. A.; Cozzi, P. G.; Guiry, P. J Adv Synth Catal 2006, 348, 551;
59. (i) Xia, G.; Yamamoto, H. J Am Chem Soc 2006, 128, 2554;
60. (j) Rozners, E.; Fontanez, J. Lett Org Chem 2005, 2, 524;
61. (k) Lee, J. Y.; Miller, J. J.; Hamilton, S. S.; Sigman, M. S. Org Lett 2005, 7, 1837;
62. (l) Namba, K.; Kishi, Y. J Am Chem Soc 2005, 127, 15382;
63. (m) Namba, K.; Wang, J.; Cui, S.; Kishi, Y. Org Lett 2005, 7, 5421;
64. (n) Namba, K.; Cui, S.; Wang, J.; Kishi, Y. Org Lett 2005, 7, 5417;
65. (o) Schrekker, H. S.; Micskei, K.; Hajdu, C.; Patonay, T.; De Bolster, M. W. G.; Wessjohann, L. A. Adv Syn Cat 2004, 346, 731;
66. (p) Namba, K.; Kishi, Y. Org Lett 2004, 6, 5031;
67. (q) Kuroso, M.; Lin, M.-H.; Kishi, Y. J Am Chem Soc 2004, 126, 12248;
68. (r) Bandini, M.; Cozzi, P. G.; Licciulli, S.; Umani-Ronchi, A. Synthesis 2004, 409;
69. (s) Berkessel, A.; Menche, D.; Sklorz, C. A.; Schrcder, M.; Paterson, I. Angew Chem Int Ed 2003, 42, 1032;
70. (t) Wan, Z.-K.; Choi, H.-W.; Kang, F.-A.; Nakajima, K.; Demeke, D.; Kishi, Y. Org Lett 2002, 4, 4431;
71. (u) Choi, H. W.; Nakajima, K.; Demeke, D.; Kang, F.-A.; Jun, H.-S.; Wan, Z.-K.; Kishi, Y. Org Lett 2002, 4, 4435.