Highly enantioselective copper-catalyzed ring opening of oxabicyclic alkenes with Grignard reagents

Chemistry - An Asian Journal

Volumn 3, Issue 12, 2008, Pages 2105-2111

  Zhang, Wei ^a   Zhu, Shou Fei ^a   Qiao, Xiang Chen ^a   Zhou, Qi Lin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; Copper; Enantioselectivity; Grignard reaction; Spiro compounds

Indexed keywords

EID: 57349181400     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800159     Document Type: Article

References (75)

1. a) Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
2. b) K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196;
3. c) S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763-2793;
4. d) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829-2844.
5. B. L. Feringa, A. H. M. de Vries in Advances in Catalytic Processes: Asymmetric Chemical Transformations, Vol. 1 (Ed.: M. P. Doyle), JAI, Greenwich, CT, 1995, 151-192.
6. a) T. Hayashi, K. Hayashizaki, T. Kiyoi, Y. Ito, J. Am. Chem. Soc. 1988, 110, 8153-8156;
7. b) T. Shimada, Y.-H. Cho, T. Hayashi, J. Am. Chem. Soc. 2002, 124, 13396-13397.
8. a) J. P. Morken, M. T. Didiuk, A. H. Hoveyda, J. Am. Chem. Soc. 1993, 115, 6997-6998;
9. b) M. T. Didiuk, C. W. Johannes, J. P. Morken, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 7097-7104;
10. c) M. S. Visser, N. M. Heron, M. T. Didiuk, J. F. Sagal, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 4291-4298.
11. a) B. L. Feringa, R. Badorrey, D. Peňa, S. R. Harutyunyan, A. J. Minnaard, Proc. Natl. Acad. Sci. USA 2004, 101, 5834-5838;
12. b) F. López, S. R. Harutyunyan, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2004, 126, 12784-12785.
13. K. Tissot-Croset, D. Polet, A. Alexakis, Angew. Chem. 2004, 116, 2480-2482;
14. Angew. Chem. Int. Ed. 2004, 43, 2426-2428.
15. For recent reviews on transition-metal-catalyzed enantioselective conjugate reactions and allylic alkylation with Grignard reagents, see: a) S. Woodward, Angew. Chem. 2005, 117, 5696-5698;
16. Angew. Chem. Int. Ed. 2005, 44, 5560-5562;
17. b) H. Yorimitsu, K. Oshima, Angew. Chem. 2005, 117, 4509-4513;
18. Angew. Chem. Int. Ed. 2005, 44, 4435-4439;
19. c) F. López, A. J. Minnaard, B. L. Feringa, Acc. Chem. Res. 2007, 40, 179-188;
20. For copper-catalyzed enantioselective conjugate reaction with Grignard reagents, also see: d) F. López, S. R. Harutyunyan, A. Meetsma, A. J. Minnaard, B. L. Feringa, Angew. Chem. 2005, 117, 2812-2816;
21. Angew. Chem. Int. Ed. 2005, 44, 2752-2756;
22. e) R. D. Mazery, M. Pullez, F. López, S. R. Harutyunyan, A. Meetsma, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2005, 127, 9966-9967;
23. f) D. Martin, S. Kehrli, M. d'Augustin, H. Clavier, M. Mauduit, A. Alexakis, J. Am. Chem. Soc. 2006, 128, 8416-8417;
24. g) S. R. Harutyunyan, F. López, W. R. Browne, A. Correa, D. Peňa, R. Badorrey, A. Meetsma, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2006, 128, 9103-9118;
25. h) G. P. Howell, S. P. Fletcher, K. Geurts, B. ter Horst, B. L. Feringa, J. Am. Chem. Soc. 2006, 128, 14977-14985;
26. i) S.-Y. Wang, S.-J. Ji, T.-P. Loh, J. Am. Chem. Soc. 2007, 129, 276-277;
27. For copper-catalyzed enantioselective allylic alkylation with Grignard reagents, also see: j) F. López, A. W. van Zijl, A. J. Minnaard, B. L. Feringa, Chem. Commun. 2006, 409-411;
28. k) C. A. Falciola, K. Tissot-Croset, A. Alexakis, Angew. Chem. 2006, 118, 6141-6144;
29. Angew. Chem. Int. Ed. 2006, 45, 5995-5998;
30. l) K. Geurts, S. P. Fletcher, B. L. Feringa, J. Am. Chem. Soc. 2006, 128, 15572-15573;
31. m) A. W. van Zijl, F. López, A. J. Minnaard, B. L. Feringa, J. Org. Chem. 2007, 72, 2558-2563.
32. For Lewis base-catalyzed enantioselective allylic alkylation with Grignard reagents, see: a) Y. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2006, 128, 15604-15605;
33. For copper-catalyzed kinetic resolution of 1,3-cyclohexadiene monoepoxide with Grignard reagents, see b) R. Millet, A. Alexakis, Synlett 2007, 435-438.
34. For reviews, see: a) M. Lautens, Synlett 1993, 177-185;
35. b) M. Lautens, K. Fagnou, S. Hiebert, Acc. Chem. Res. 2003, 36, 48-58;
36. c) M. Pineschi, New J. Chem. 2004, 28, 657-665.
37. a) M. Lautens, J. L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804-1805;
38. b) M. Lautens, S. Hiebert, J. L. Renaud, J. Am. Chem. Soc. 2001, 123, 6834-6839;
39. c) M. Lautens, S. Hiebert, J. Am. Chem. Soc. 2004, 126, 1437-1447;
40. d) M. Li, X.-X. Yan, W. Hong, X.-Z. Zhu, B.-X. Cao, J. Sun, X.-L. Hou, Org. Lett. 2004, 6, 2833-2835;
41. e) S. Cabrera, R. G. Arrayás, J. C. Carretero, Angew. Chem. 2004, 116, 4034-4037;
42. Angew. Chem. Int. Ed. 2004, 43, 3944-3947;
43. f) S. Cabrera, R. G. Arrayás, I. Alonso, J. C. Carretero, J. Am. Chem. Soc. 2005, 127, 17938-17947;
44. g) T. Imamoto, K. Sugita, K. Yoshida, J. Am. Chem. Soc. 2005, 127, 11934-11935;
45. h) F. Bertozzi, M. Pineschi, F. Macchia, L. A. Arnold, A. J. Minnaard, B. L. Feringa, Org. Lett. 2002, 4, 2703-2705.
46. a) M. Lautens, T. Rovis, N. D. Smith, D. Ostrovsky, Pure. Appl. Chem. 1998, 70, 1059-1064;
47. b) M. Lautens, P. Chiu, S. Ma, T. Rovis, J. Am. Chem. Soc. 1995, 117, 532-533;
48. c) M. Lautens, T. Rovis, J. Am. Chem. Soc. 1997, 119, 11090-11091;
49. d) D. B. Millward, G. Sammis, R. M. Waymouth, J. Org. Chem. 2000, 65, 3902-3909.
50. a) M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki, Org. Lett. 2002, 4, 1311-1314;
51. b) M. Lautens, C. Dockendorff, Org. Lett. 2003, 5, 3695-3698.
52. a) M. Lautens, S. Ma, J. Org. Chem. 1996, 61, 7246-7247;
53. b) M. Nakamura, A. Hirai, E. Nakamura, J. Am. Chem. Soc. 2000, 122, 978-979;
54. c) M. Nakamura, K. Matsuo, T. Inoue, E. Nakamura, Org. Lett. 2003, 5, 1373-1375;
55. d) R. G. Arrayas, S. Cabrera, J. C. Carretero, Org. Lett. 2003, 5, 1333-1336;
56. e) R. G. Arrayas, S. Cabrera, J. C. Carretero, Synthesis 2006, 1205-1219;
57. f) R. G. Arrayas, S. Cabrera, J. C. Carretero, Org. Lett. 2005, 7, 219-221.
58. W. Zhang, L.-X. Wang, W.-J. Shi, Q.-L. Zhou, J. Org. Chem. 2005, 70, 3734-3736.
59. S.-F. Zhu, Y. Yang, W.-L. Wang, B. Liu, Q.-L. Zhou, Org. Lett. 2005, 7, 2333-2335.
60. B. Liu, S.-F. Zhu, W. Zhang, C. Chen, Q.-L. Zhou, J. Am. Chem. Soc. 2007, 129, 5834-5835.
61. A. Cote, J. N. Desrosiers, A. A. Boezio, A. B. Charette, Org. Synth. 2006, 83, 1-4.
62. Reaction time: 15 h; yield: 85%; trans/cis: 97/3; ee: 56%. See Ref. [14].
63. The configuration of the ring-opening product 10 (1R, 2S) is determined by a comparison of optical rotation with that in literature, see: Ref. [10 h].
64. E. M. Vogl, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 1672-1680;
65. Angew. Chem. Int. Ed. 1999, 38, 1570-1577.
66. D. A. Evans, S. J. Miller, T. Lectka, P. von Matt, J. Am. Chem. Soc. 1999, 121, 7559-7573.
67. For review on NaBArF, see: a) I. Krossing, I. Raabe, Angew. Chem. 2004, 116, 2116-2142;
68. Angew. Chem. Int. Ed. 2004, 43, 2066-2090;
69. For application of NaBArF in hydrogenation, see: b) A. Lightfoot, P. Schnider, A. Pfaltz, Angew. Chem. 1998, 110, 3047-3050;
70. Angew. Chem. Int. Ed. 1998, 37, 2897-2899;
71. c) A. Pfaltz, J. Blankenstein, R. Hilgraf, E. Hörmann, S. McIntyre, F. Menges, M. Schönleber, S. P. Smidt, B. Wüstenberg, N. Zimmermann, Adv. Synth. Catal. 2003, 345, 33-43;
72. d) K. Makino, M. Iwasaki, Y. Hamada, Org. Lett. 2006, 8, 4573-4576;
73. For application of NaBArF in copper-catalyzed carbenoids-insertion reactions, see: Ref. [16], and e) C. Chen. S.-F. Zhu, B. Liu, L.-X. Wang, Q.-L. Zhou, J. Am. Chem. Soc. 2007, 129, 12616-12617;
74. f) S.-F. Zhu, C. Chen, Y. Cai, Q.-L. Zhou, Angew. Chem. 2008, 120, 946-948;
75. Angew. Chem. Int. Ed. 2008, 47, 932-934. For application of NaBArF in Pd-catalyzed ring-opening reaction, see: Refs. [10e] and [10f].