Nickel-catalyzed enantio- and diastereoselective three-component coupling of 1,3-dienes, aldehydes, and a silylborane leading to α-chiral allylsilanes

Angewandte Chemie - International Edition

Volumn 51, Issue 5, 2012, Pages 1228-1231

  Saito, Nozomi ^a   Kobayashi, Ayami ^a   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

aldehydes; asymmetric catalysis; dienes; nickel; silylborane

Indexed keywords

1 ,3-DIENES; ALLYLSILANES; ASYMMETRIC CATALYSIS; BOND METATHESIS; DIASTEREOSELECTIVE; DIENES; ENANTIO; ENANTIOSELECTIVE; SILYLBORANE; THREE-COMPONENT COUPLING;

ALDEHYDES; CATALYSIS; NICKEL; ORGANIC COMPOUNDS;

OLEFINS;

ALDEHYDE; ALKENE; BORANE DERIVATIVE; HETEROCYCLIC COMPOUND; NICKEL; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALKENES; BORANES; CATALYSIS; HETEROCYCLIC COMPOUNDS; NICKEL; SILANES; STEREOISOMERISM;

EID: 84856155852     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201107360     Document Type: Article

References (74)

1. I. Beletskaya, C. Moberg, Chem. Rev. 1999, 99, 3435
2. L.-B. Han, M. Tanaka, Chem. Commun. 1999, 395
3. Y. Ito, J. Organomet. Chem. 1999, 576, 300
4. M. Suginome, Y. Ito, Chem. Rev. 2000, 100, 3221
5. M. Suginome, Y. Ito, J. Organomet. Chem. 2003, 680, 43
6. T. Ishiyama, N. Miyaura, Chem. Rec. 2004, 3, 271
7. I. Beletskaya, C. Moberg, Chem. Rev. 2006, 106, 2320
8. T. Ohmura, M. Suginome, Bull. Chem. Soc. Jpn. 2009, 82, 29
9. C. Pubill-Ulldemolins, A. Bonet, C. Bo, H. Gulyás, E. Fernández, Org. Biomol. Chem. 2010, 8, 2667.
10. M. Suginome, T. Matsuda, Y. Ito, Organometallics 1998, 17, 5233; for the Ni-catalyzed silastannylative coupling of 1,3-dienes and aldehydes, see
11. Y. Sato, N. Saito, M. Mori, Chem. Lett. 2003, 32, 18
12. N. Saito, M. Mori, Y. Sato, J. Organomet. Chem. 2007, 692, 460; for the Ni-catalyzed diborative coupling of 1,3-dienes and aldehydes, see
13. H. Y. Cho, J. P. Morken, J. Am. Chem. Soc. 2008, 130, 16140
14. H. Y. Cho, J. P. Morken, J. Am. Chem. Soc. 2010, 132, 7576.
15. Y. Takemoto, H. Miyabe, in Catalytic Asymmetric Synthesis, 3 rd ed., (Ed.: I. Ojima,), Wiley, Hoboken, NJ, 2010, pp. 227-267, and references therein
16. H. E. Burks, J. P. Morken, Chem. Commun. 2007, 4717, and references therein; for recent examples, see
17. H. E. Burks, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 9134
18. L. T. Kliman, S. N. Mlynarski, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 13210.
19. Morken reported a platinum-catalyzed diboration of 1,3-dienes with a chiral diboron reagent followed by asymmetric allylboration of aldehydes; see:, J. B. Morgan, J. P. Morken, Org. Lett. 2003, 5, 2573.
20. M. Kimura, Y. Tamaru, In Modern Organonickel Chemistry (Ed.:, Y. Tamaru,), Wiley-Weinheim, 2005, pp. 137-170
21. Y. Tamaru, J. Organomet. Chem. 1999, 576, 215
22. S. Ikeda, Angew. Chem. 2003, 115, 5276
23. Angew. Chem. Int. Ed. 2003, 42, 5120
24. J. Montgomery, Angew. Chem. 2004, 116, 3980
25. Angew. Chem. Int. Ed. 2004, 43, 3890.
26. F. Shibahara, J. F. Bower, M. J. Krische, J. Am. Chem. Soc. 2008, 130, 6338
27. M. Kimura, D. Nojiri, M. Fukushima, S. Oi, Y. Sonoda, Y. Inoue, Org. Lett. 2009, 11, 3794
28. M. Fukushima, D. Takushima, M. Kimura, J. Am. Chem. Soc. 2010, 132, 16346.
29. Y. Sato, M. Takimoto, K. Hayashi, T. Katsuhara, K. Takagi, M. Mori, J. Am. Chem. Soc. 1994, 116, 9771
30. Y. Sato, M. Takimoto, M. Mori, Tetrahedron Lett. 1996, 37, 887
31. Y. Sato, M. Takimoto, M. Mori, Synlett 1997, 734
32. Y. Sato, N. Saito, M. Mori, Tetrahedron Lett. 1997, 38, 3931
33. Y. Sato, N. Saito, M. Mori, Tetrahedron 1998, 54, 1153
34. M. Takimoto, Y. Hiraga, Y. Sato, M. Mori, Tetrahedron Lett. 1998, 39, 4543
35. Y. Sato, M. Takimoto, M. Mori, J. Am. Chem. Soc. 2000, 122, 1624
36. Y. Sato, N. Saito, M. Mori, J. Am. Chem. Soc. 2000, 122, 2371
37. Y. Sato, M. Takimoto, M. Mori, Chem. Pharm. Bull. 2000, 48, 1753
38. Y. Sato, N. Saito, M. Mori, J. Org. Chem. 2002, 67, 9310.
39. Y. Sato, T. Takanashi, M. Hoshiba, M. Mori, Tetrahedron Lett. 1998, 39, 5579
40. Y. Sato, T. Takanashi, M. Mori, Organometallics 1999, 18, 4891
41. Y. Sato, T. Takanashi, M. Hoshiba, M. Mori, J. Organomet. Chem. 2003, 688, 36; see also, Refs [7g,h, and j]; for intermolecular couplings via oxanickelacycle intermediates, see
42. Y. Sato, R. Sawaki, N. Saito, M. Mori, J. Org. Chem. 2002, 67, 656
43. Y. Sato, R. Sawaki, M. Mori, Organometallics 2001, 20, 5510
44. R. Sawaki, Y. Sato, M. Mori, Org. Lett. 2004, 6, 1131
45. Y. Sato, Y. Hinata, R. Seki, Y. Oonishi, N. Saito, Org. Lett. 2007, 9, 5597
46. N. Saito, T. Yamazaki, Y. Sato, Tetrahedron Lett. 2008, 49, 5073
47. N. Saito, T. Yamazaki, Y. Sato, Chem. Lett. 2009, 38, 594.
48. S. Ogoshi, K.-i. Tonomori, M.-a. Oka, H. Kurosawa, J. Am. Chem. Soc. 2006, 128, 7077.
49. M. Kimura, A. Ezoe, K. Shibata, Y. Tamaru, J. Am. Chem. Soc. 1998, 120, 4033
50. M. Kimura, H. Fujimatsu, A. Ezoe, K. Shibata, M. Shimizu, S. Matsumoto, Y. Tamaru, Angew. Chem. 1999, 111, 410
51. Angew. Chem. Int. Ed. 1999, 38, 397
52. M. Kimura, A. Ezoe, S. Tanaka, Y. Tamaru, Angew. Chem. 2001, 113, 3712
53. Angew. Chem. Int. Ed. 2001, 40, 3600
54. K. Shibata, M. Kimura, M. Shimizu, Y. Tamaru, Org. Lett. 2001, 3, 2181
55. M. Kimura, A. Ezoe, M. Mori, K. Iwata, Y. Tamaru, J. Am. Chem. Soc. 2006, 128, 8559; see also, ref. [8d]; for alkylative coupling, see
56. M. Kimura, S. Matsuo, K. Shibata, Y. Tamaru, Angew. Chem. 1999, 111, 3586
57. Angew. Chem. Int. Ed. 1999, 38, 3386; see also Refs [2b-e] and [9].
58. K.-S. Lee, A. H. Hoveyda, J. Am. Chem. Soc. 2010, 132, 2898
59. D. Li, T. Tanaka, H. Ohmiya, M. Sawamura, Org. Lett. 2010, 12, 3344
60. V. K. Aggarwal, M. Binanzer, M. C. de Ceglie, M. Gallanti, B. W. Glasspoole, S. J. F. Kendrick, R. P. Sonawane, A. Vázquez-Romero, M. P. Webster, Org. Lett. 2011, 13, 1490
61. K. Fukuda, M. Miyashita, K. Tanino, Tetrahedron Lett. 2010, 51, 4523.
62. M. Suginome, T. Matsuda, Y. Ito, Organometallics 2000, 19, 4647.
63. M. Suginome, T. Ohmura, Y. Miyake, S. Mitani, Y. Ito, M. Murakami, J. Am. Chem. Soc. 2003, 125, 11174
64. M. Gerdin, C. Moberg, Adv. Synth. Catal. 2005, 347, 749
65. T. Ohmura, H. Taniguchi, M. Suginome, J. Am. Chem. Soc. 2006, 128, 13682
66. T. Ohmura, H. Taniguchi, Y. Kondo, M. Suginome, J. Am. Chem. Soc. 2007, 129, 3518
67. M. Gerdin, M. Penhoat, R. Zalubovskis, C. Pétermann, C. Moberg, J. Organomet. Chem. 2008, 693, 3519.
68. Ito reported a platinum-catalyzed silaborative coupling of 1,3-dienes and aldehydes through the formation of C-C, C-B, and O-Si bonds in one pot; see:, M. Suginome, H. Nakamura, T. Matsuda, Y. Ito, J. Am. Chem. Soc. 1998, 120, 4248.
69. Y. Uozumi, T. Hayashi, J. Am. Chem. Soc. 1991, 113, 9887
70. M. J. Burk, J. E. Feaster, R. L. Harlow, Organometallics 1990, 9, 2653
71. E. Keller, J. Maurer, R. Naasz, T. Schader, A. Meetsma, B. L. Feringa, Tetrahedron: Asymmetry 1998, 9, 2409
72. L. A. Arnold, R. Imbos, A. Mandoli, A. H. M. de Vries, R. Naasz, B. L. Feringa, Tetrahedron 2000, 56, 2865
73. F. Zhang, Q.-H. Fan, Org. Biomol. Chem. 2009, 7, 4470.
74. For an enantioselective reductive coupling of 1,3-dienes and aldehydes using a chiral phosphoramidite ligand, see:, Y. Yang, S.-F. Zhu, H.-F. Duan, C.-Y. Zhou, L.-X. Wang, Q.-L. Zhou, J. Am. Chem. Soc. 2007, 129, 2248.