Catalytic asymmetric epoxidation of α,β-unsaturated esters with chiral yttrium-biaryldiol complexes

Chemistry - An Asian Journal

Volumn 2, Issue 2, 2007, Pages 257-264

  Kakei, Hiroyuki ^a   Tsuji, Riichiro ^a   Ohshima, Takashi ^a   Morimoto, Hiroyuki ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Epoxidation; Rare earth metals; Yttrium

Indexed keywords

EPOXIDE; ESTER; OXAZINE DERIVATIVE; PHENYLPROPIONIC ACID DERIVATIVE; RAGAGLITAZAR; YTTRIUM;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; EPOXY COMPOUNDS; ESTERS; OXAZINES; PHENYLPROPIONATES; STEREOISOMERISM; YTTRIUM;

EID: 34248189099     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200600309     Document Type: Article

References (72)

1. For recent general reviews on asymmetric epoxidations, see: a) Modern Oxidation Methods (Ed.: J. E. Bäckvall), Wiley-VCH, Weinheim, 2004;
2. b) C. Bonini, G. Righi, Tetrahedron 2002, 55, 4981;
3. c) Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su, Chem. Rev. 2005, 105, 1603;
4. d) E. M. McGarrigle, D. G. Gilheany, Chem. Rev. 2005, 105, 1563, and references therein.
5. For recent general reviews on asymmetric epoxidation of electron-deficient C=C bonds, see: a) M. J. Porter, J. Skidmore, Chem. Commun. 2000, 1215;
6. b) T. Nemoto, T. Ohshima, M. Shibasaki, J. Synth. Org. Chem. Jpn. 2002, 60, 94.
7. a) R. Helder, J. C. Hummelen, R. W. P. M. Laane, J. S. Wiering, H. Wynberg, Tetrahedron Lett. 1976, 17, 1831;
8. b) S. Julia, J. Masana, J. C. Vega, Angew. Chem. 1980, 92, 968;
9. Angew. Chem. Int. Ed. Engl. 1980, 19, 929; for other examples, see reviews in reference [2].
10. For reviews of catalyzed asymmetric epoxidations with chiral ketones, see: a) S. E. Denmark, Z. Wu, Synlett 1999, 847;
11. b) M. Frohn, Y. Shi, Synthesis 2000, 1979;
12. c) Y. Shi, Acc. Chem. Res. 2004, 37, 488;
13. d) D. Yang, Acc. Chem. Res. 2004, 37, 497; for reviews of poly(amino acid)-catalyzed asymmetric epoxidation, see:
14. e) C. Lauret, S. M. Roberts, Aldrichimica Acta 2002, 35, 47;
15. f) D. R. Kelly, S. M. Roberts, Biopolymers 2006, 84, 74; for other examples of asymmetric epoxidation of enones, see reviews in references [1,2].
16. a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329;
17. b) T. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2725; see also:
18. c) K. Daikai, M. Kamaura, J. Inanaga, Tetrahedron Lett. 1998, 39, 7321;
19. d) K. Daikai, T. Hayano, R. Kino, H. Furuno, T. Kagawa, J. Inanaga, Chirality 2003, 15, 83;
20. e) R. Kino, K. Daikai, T. Kawanami, H. Furuno, J. Inanaga, Org. Biomol. Chem. 2004, 2, 1822.
21. a) E. N. Jacobsen, W. Zhang, A. R. Muci, J. R. Ecker, L. Deng, J. Am. Chem. Soc. 1991, 113, 7063;
22. b) L. Deng, E. N. Jacobsen, J. Org. Chem. 1992, 57, 4320;
23. c) E. N. Jacobsen, L. Deng, Y. Furukawa, L. E. Martínez, Tetrahedron 1994, 50, 4323.
24. a) Z. X. Wang, Y. Shi, J. Org. Chem. 1997, 62, 8622;
25. b) X.-Y. Wu, X. She, Y. Shi, J. Am. Chem. Soc. 2002, 124, 8792;
26. c) M. Seki, T. Furutani, R. Imashiro, T. Kuroda, T. Yamanaka, N. Harada, H. Arakawa, M. Kusama, T. Hashiyama, Tetrahedron Lett. 2001, 42, 8201;
27. d) T. Furutani, R. Imashiro, M. Hatsuda, M. Seki, J. Org. Chem. 2002, 67, 4599;
28. e) A. Armstrong, B. R. Hayter, Chem. Commun. 1998, 621;
29. f) A. Solladié-Cavallo, L. Bouérat, Org. Lett. 2000, 2, 3531;
30. g) A. Solladié-Cavallo, L. Bouérat, L. Jierry, Eur. J. Org. Chem. 2001, 4557; for chiral ketone catalyst used in references [7c,d], see reference [4d].
31. a) T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9474;
32. b) T. Ohshima, T. Nemoto, S.-y. Tosaki, H. Kakei, V. Gnanadesikan, M. Shibasaki, Tetrahedron 2003, 59, 10485.
33. a) T. Nemoto, H. Kakei, V. Gnanadesikan, S.-y. Tosaki, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2002, 124, 14544;
34. b) S.-y. Tosaki, T. Nemoto, T. Ohshima, M. Shibasaki, Org. Lett. 2003, 5, 495.
35. a) T. Kinoshita, S. Okada, S.-R. Park, S. Matsunaga, M. Shibasaki, Angew. Chem. 2003, 115, 4828;
36. Angew. Chem. Int. Ed. 2003, 42, 4680;
37. b) S. Matsunaga, T. Kinoshita, S. Okada, S. Harda, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 7559;
38. c) S. Matsunaga, H. Qin, M. Sugita, S. Okada, T, Kinoshita, N. Yamagiwa, M. Shibasaki, Tetrahedron 2006, 62, 6630.
39. E. Weitz, A. Scheffer, Ber. Dtsch. Chem. Ges. 1921, 54, 2327.
40. A portion of this article was previously reported as a preliminary communication: H. Kakei, R. Tsuji, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 8962.
41. For recent reviews of bifunctional asymmetric catalysis, see: a) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 1702, 2187;
42. b) J.-A. Ma, D. Cahard, Angew. Chem. 2004, 116, 4666;
43. Angew. Chem. Int. Ed. 2004, 43, 4566;
44. c) M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491;
45. d) M. Shibasaki, S. Matsunaga, Chem. Soc. Rev. 2006, 35, 269.
46. For mechanistic studies of epoxidation catalyzed by RE-binol complexes, see reference [5b].
47. 8-binol, see: T. T.-L. Au-Yeung; S.-S. Chan, A. S. C. Chan, Adv. Synth. Catal. 2003, 345, 537.
48. For synthesis of 6,6′-disubstituted 2,2′-biphenyldiols, see: a) T. Harada, T. M. T. Tuyet, A. Oku, Org. Lett. 2000, 2, 1319;
49. b) T. Harada, S. Ueda, T. Yoshida, A. Inoue, M. Takeuchi, N. Ogawa, A. Oku, J. Org. Chem. 1994, 59, 7575;
50. c) T. Harada, T. Yoshida, A. Inoue, M. Takeuchi, A. Oku, Synlett 1995, 283;
51. d) T. Harada, S. Ueda, T. M. T. Tuyet, A. Inoue, K. Fujita, M. Takeuchi, N. Ogawa, A. Oku, M. Shiro, Tetrahedron 1997, 53, 16663;
52. e) T. Harada, T. M. T. Tuyet, K. Hashimoto, M. Hatsuda, A. Oku, Synlett 1997, 1426;
53. f) T. M. T. Tuyet, T. Harada, K. Hashimoto, M. Hatsuda, A. Oku, J. Org. Chem. 2000, 65, 1335.
54. For properties of 6,6′-disubstituted 2,2′-biphenyldiols, see: a) T. Harada, M. Takeuchi, M. Hatsuda, H. Ueda, A. Oku, Tetrahedron: Asymmetry 1996, 7, 2479;
55. b) D. Gao, S. Schefzick, K. B. Lipkowitz, J. Am. Chem. Soc. 1999, 121, 9481.
56. For related examples of heteroatom linker effects on chiral binaphthol ligands, see: a) S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252;
57. b) N. Kumagai, S. Matsunaga, T. Kinoshita, S. Harada, S. Okada, S. Sakamoto, K. Yamaguchi, M. Shibasaki. J. Am. Chem. Soc. 2003, 125, 2169;
58. c) K. Majima, R. Takita, A. Okada, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 15837, and references therein; see also the review:
59. d) M. Shibasaki, S. Matsunaga, Chem. Soc. Rev. 2006, 35, 269.
60. Previous mechanistic studies suggested that the concentration of the catalyst is important to maximize the formation of the active species in equilibrium; see reference [5b]. Similar effects were observed in asymmetric epoxidations in which a samarium complex was used; see reference [10].
61. +) observed by use of tandem mass spectrometry (M=rare-earth metal, hmpa = hexamethylphosphoramide); see: a) H. Tsuruta, K. Yamaguchi, T. Imamoto, Chem. Commun. 1999, 1703;
62. b) H. Tsuruta, K. Yamaguchi, T. Imamoto, Tetrahedron 2003, 59, 10419.
63. 3 of the same quality is also available from Aldrich. See also: M. Shibasaki, M. Kanai, S. Matsunaga, Aldrichimica Acta 2006, 39, 31.
64. 3P(O) system. The reaction of 2r gave 3r in 87% yield (24 h) and 97% ee with 4-Å molecular sieves (Table 8, entry 1, 10 mol% catalyst), 52% yield (30 h) and 90% ee with 3-Å molecular sieves, 76% yield (30 h) and 93% ee with 5-Å molecular sieves, 8% yield (30 h) and 97% ee with MS 13X, and 14% yield (30 h) and 85% ee without molecular sieves.
65. 3P(O) is required. For a discussion, see references [5b,c].
66. For stereoselective synthesis of (-)-ragaglitazar, see: a) B. B. Lohray, V. B. Lohray, A. C. Bajji, S. Kalchar, R. R. Poondra, S. Padakanti, R. Chakrabarti, R. K. Vikramadithyan, P. Misra, S. Juluri, N. V. S. R. Mamidi, R. Rajagopalan, J. Med. Chem. 2001, 44, 2675;
67. b) H. Deussen, M. Zundel, M. Valdois, S. V. Lehmann, V. Weil, C. M. Hjort, P. R. Østergaard, E. Marcussen, S. Ebdrup, Org. Process Res. Dev. 2003, 7, 82;
68. c) S. Edbrup, I. Pettersson, H. B. Rasmussen, H.-J. Deussen, A. F. Jensen, S. B. Mortensen, J. Fleckner, L. Pridal, L. Nygaard, P. Sauerberg, J. Med. Chem. 2003, 46, 1306;
69. d) M. B. Audrus, E. J. Hicken, J. C. Stephens, D. K. Bedke, J. Org. Chem. 2005, 70, 9470.
70. For the biological characterization of ragaglitazar, see: a) P. Sauerberg, I. Petterson, L. Jeppesen, P. S. Bury, J. P. Mogensen, K. Wasserman, C. L. Brand, J. Sturis, H. F. Wöldike, J. Fleckner, A.-S. T. Andersen, S. B. Mortensen, L. A. Svensson, H. B. Rasmussen, S. V. Lehmann, Z. Polivka, K. Sindelar, V. Panajotpva, L. Ynddal, E. M. Wullf, J. Med. Chem. 2002, 45, 789;
71. b) B. K. Skrumsager, K. K. Nielsen, M. Muller, G. Pabst, P. G. Drake, B. Edsberg, J. Clin. Pharmacol. 2003, 43, 1244.
72. The enantiomeric excess was determined after epoxide-ring opening; see Supporting Information.