Highly enantioselective rhodium-catalyzed asymmetric 1,4-addition reactions of arylboronic acids to acyclic α,β-unsaturated compounds: The formal synthesis of (-)-indatraline

Chemistry - A European Journal

Volumn 17, Issue 41, 2011, Pages 11405-11409

  Wei, Wei Ting ^a   Yeh, Jiann Yih ^a   Kuo, Ting Shen ^a   Wu, Hsyueh Liang ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

addition reactions; arylboronic acids; asymmetric catalysis; diene ligands; enantioselectivity; indatraline; rhodium

Indexed keywords

1 ,4-ADDITION; ARYLBORONIC ACIDS; ASYMMETRIC CATALYSIS; CATALYTIC LOADING; DIENE LIGANDS; ENANTIOSELECTIVE; FORMAL SYNTHESIS; IN-SITU; INDATRALINE; RHODIUM-CATALYZED; TOTAL SYNTHESIS;

ADDITION REACTIONS; CATALYSIS; ENANTIOSELECTIVITY; LIGANDS; OLEFINS; RHODIUM; RHODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

UNSATURATED COMPOUNDS;

BORONIC ACID DERIVATIVE; INDAN DERIVATIVE; INDATRALINE; METHYLAMINE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BORONIC ACIDS; CATALYSIS; INDANS; METHYLAMINES; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM;

EID: 80053211491     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102073     Document Type: Article

References (89)

1. W. C. Zeise, Poggendorffs Ann. Phys. 1827, 9, 632-633.
2. M. A. Bennett, Chem. Rev. 1962, 62, 611-652
3. E. O. Fischer, H. Werner, Angew. Chem. 1963, 75, 57-70
4. Angew. Chem. Int. Ed. Engl. 1963, 2, 80-93
5. R. Jones, Chem. Rev. 1968, 68, 785-806
6. F. R. Hartley, Angew. Chem. 1972, 84, 657-667
7. Angew. Chem. Int. Ed. Engl. 1972, 11, 596-606
8. S. D. Ittel, J. A. Ibers, Adv. Organomet. Chem. 1976, 14, 33-61
9. I. Omae, Angew. Chem. 1982, 94, 902-915
10. Angew. Chem. Int. Ed. Engl. 1982, 21, 889-902
11. Comprehensive Organometallic Chemistry II (Eds.:, E. W. Abel, F. G. A. Stone, G. Wilkinson,), Pergamon, Oxford, 1995
12. L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, 2 nd ed., University Science Books, Sausalito, 1999
13. Applied Homogeneous Catalysis with Organometallic Compounds, 2 nd ed., (Eds.: B. Cornils; W. A. Herrmann,), Wiley-VCH, Weinheim, 2002
14. The Organometallic Chemistry of the Transition Metals, 5 th ed., (Ed.: R. H. Crabtree,), Wiley, New York, 2009.
15. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994
16. J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995
17. Comprehensive Asymmetric Catalysis, Vol. 1-3 (Eds.:, E. N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin, 1999
18. Catalytic Asymmetric Synthesis, 2 nd ed., (Ed.: I. Ojima,), Wiley, New York, 2000.
19. T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc. 2003, 125, 11508-11509
20. R. Shintani, K. Ueyama, I. Yamada, T. Hayashi, Org. Lett. 2004, 6, 3425-3427
21. N. Tokunaga, Y. Otomaru, K. Okamoto, K. Ueyama, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2004, 126, 13584-13585
22. Y. Otomaru, N. Tokunaga, R. Shintani, T. Hayashi, Org. Lett. 2005, 7, 307-310
23. R. Shintani, K. Okamoto, Y. Otomaru, K. Ueyama, T. Hayashi, J. Am. Chem. Soc. 2005, 127, 54-55
24. Y. Otomaru, K. Okamoto, R. Shintani, T. Hayashi, J. Org. Chem. 2005, 70, 2503-2508
25. R. Shintani, A. Tsurusaki, K. Okamoto, T. Hayashi, Angew. Chem. 2005, 117, 3977-3980
26. Angew. Chem. Int. Ed. 2005, 44, 3909-3912
27. R. Shintani, K. Okamoto, T. Hayashi, Org. Lett. 2005, 7, 4757-4759
28. A. Kina, K. Ueyama, T. Hayashi, Org. Lett. 2005, 7, 5889-5892
29. F.-X. Chen, A. Kina, T. Hayashi, Org. Lett. 2006, 8, 341-344
30. R. Shintani, W.-L. Duan, T. Hayashi, J. Am. Chem. Soc. 2006, 128, 5628-5629
31. G. Berthon-Gelloz, T. Hayashi, J. Org. Chem. 2006, 71, 8957-8960
32. R. Shintani, K. Takatsu, T. Hayashi, Angew. Chem. 2007, 119, 3809-3811
33. Angew. Chem. Int. Ed. 2007, 46, 3735-3737
34. R. Shintani, Y. Ichikawa, T. Hayashi, J. Chen, Y. Nakao, T. Hiyama, Org. Lett. 2007, 9, 4643-4645
35. R. Shintani, Y. Sannohe, T. Tsuji, T. Hayashi, Angew. Chem. 2007, 119, 7415-7418
36. Angew. Chem. Int. Ed. 2007, 46, 7277-7280
37. S. Sörgel, N. Tokunaga, K. Sasaki, K. Okamoto, T. Hayashi, Org. Lett. 2008, 10, 589-592
38. K. Okamoto, T. Hayashi, V. H. Rawal, Org. Lett. 2008, 10, 4387-4389
39. R. Shintani, Y. Tsutsumi, M. Nagaosa, T. Nishimura, T. Hayashi, J. Am. Chem. Soc. 2009, 131, 13588-13589
40. K. Okamoto, T. Hayashi, V. H. Rawal, Chem. Commun. 2009, 4815-4817
41. T. Nishimura, J. Wang, M. Nagaosa, K. Okamoto, R. Shintani, F.-Y. Kwong, W.-Y. Yu, A. S. C. Chen, T. Hayashi, J. Am. Chem. Soc. 2010, 132, 464-465
42. T. Nishimura, T. Kawamoto, M. Nagaosa, H. Kumamoto, T. Hayashi, Angew. Chem. 2010, 122, 1682-1685
43. Angew. Chem. Int. Ed. 2010, 49, 1638-1641
44. R. Shintani, M. Takeda, T. Nishimura, T. Hayashi, Angew. Chem. 2010, 122, 4061-4063
45. Angew. Chem. Int. Ed. 2010, 49, 3969-3971
46. T. Nishimura, Y. Maeda, T. Hayashi, Angew. Chem. 2010, 122, 7482-7485
47. Angew. Chem. Int. Ed. 2010, 49, 7324-7327
48. T. Nishimura, H. Makino, M. Nagaosa, T. Hayashi, J. Am. Chem. Soc. 2010, 132, 12865-12867
49. R. Shintani, M. Takeda, T. Tsuji, T. Hayashi, J. Am. Chem. Soc. 2010, 132, 13168-13169.
50. C. Fischer, C. Defieber, T. Suzuki, E. M. Carreira, J. Am. Chem. Soc. 2004, 126, 1628-1629
51. C. Defieber, J.-F. Paquin, S. Serna, E. M. Carreira, Org. Lett. 2004, 6, 3873-3876
52. J.-F. Paquin, C. R. J. Stevenson, C. Defieber, E. M. Carreira, Org. Lett. 2005, 7, 3821-3824
53. J.-F. Paquin, C. Defieber, C. R. J. Stevenson, E. M. Carreira, J. Am. Chem. Soc. 2005, 127, 10850-10851.
54. For reviews, see
55. F. Glorius, Angew. Chem. 2004, 116, 3444-3446
56. Angew. Chem. Int. Ed. 2004, 43, 3364-3366
57. C. Defieber, H. Grützmacher, E. M. Carreira, Angew. Chem. 2008, 120, 4558-4579
58. Angew. Chem. Int. Ed. 2008, 47, 4482-4502
59. R. Shintani, T. Hayashi, Aldrichimica Acta. 2009, 42, 31-38.
60. For a new set of chiral dienes with the nonbridged bicyclo[3.3.0] framework, see
61. Z.-Q. Wang, C.-G. Feng, M.-H. Xu, G.-Q. Lin, J. Am. Chem. Soc. 2007, 129, 5336-5337
62. C.-G. Feng, Z.-Q. Wang, P. Tian, M.-H. Xu, G.-Q. Lin, Chem. Asian J. 2008, 3, 1511-1516
63. C.-G. Feng, Z.-Q. Wang, C. Shao, M.-H. Xu, G.-Q. Lin, Org. Lett. 2008, 10, 4101-4104
64. Li. Wang, Z.-Q. Wang, M.-H. Xu, G.-Q. Lin, Synthesis 2010, 3263-3267
65. Z.-Q. Wang, C.-G. Feng, S.-S. Zhang, M.-H. Xu, G.-Q. Lin, Angew. Chem. 2010, 122, 5916-5919
66. Angew. Chem. Int. Ed. 2010, 49, 5780-5783.
67. T. Gendrineau, O. Chuzel, H. Eijsberg, J.-P. Genet, S. Darses, Angew. Chem. 2008, 120, 7783-7786
68. Angew. Chem. Int. Ed. 2008, 47, 7669-7672
69. T. Gendrineau, J.-P. Genet, S. Darses, Org. Lett. 2009, 11, 3486-3489
70. T. Gendrineau, J.-P. Genet, S. Darses, Org. Lett. 2010, 12, 308-310
71. M. K. Brown, E. J. Corey, Org. Lett. 2010, 12, 172-175
72. Y. Luo, A. J. Carnell, Angew. Chem. 2010, 122, 2810-2814
73. Angew. Chem. Int. Ed. 2010, 49, 2750-2754
74. C. Shao, H.-J. Yu, N.-Y. Wu, C.-G. Feng, G.-Q. Lin, Org. Lett. 2010, 12, 3820-3823
75. G. Pattison, G. Piraux, H. W. Lam, J. Am. Chem. Soc. 2010, 132, 14373-14375.
76. Y. Uozumi, S.-Y. Lee, T. Hayashi, Tetrahedron Lett. 1992, 33, 7185-7188.
77. Both the instability of the phenyl analogue of ligand 1 and the facile addition of nucleophiles to the unsubstituted double bond in ligand 2 have lead to the preparation and application of the chiral diene ligands of the bicyclo[2.2.2] skeleton.
78. -1;, M. S. Allen, N. Darby, P. Salisbury, E. N. Sigurdson, T. Money, Can. J. Chem. 1979, 57, 733-741.
79. D. L. Comins, A. Dehghani, Tetrahedron Lett. 1992, 33, 6299-6302.
80. R. Itooka, Y. Iguchi, N. Miyaura, Chem. Lett. 2001, 722-723
81. R. Itooka, Y. Iguchi, N. Miyaura, J. Org. Chem. 2003, 68, 6000-6004.
82. 1H NMR experiments over several weeks.
83. The configurations of the adducts were determined by comparing the sign of the specific rotation with those of the reported samples in the literature.
84. H. M. L. Davies, T. M. Gregg, Tetrahedron Lett. 2002, 43, 4951-4953
85. J. C. Pastre, C. R. D. Correia, Adv. Synth. Catal. 2009, 351, 1217-1223
86. K. Yoo, H. Kim, J. Yun, Chem. Eur. J. 2009, 15, 11134-11138
87. J. G. Taylor, C. R. D. Correia, J. Org. Chem. 2011, 76, 857-869.
88. 2/hexane gave single crystals suitable for X-ray crystallographic analysis.
89. The overall yields of chiral dienes 3 a-h are 17-25 % from (-)-bornyl acetate as a 40 % yield of compound 4 was constantly observed. Attempts to optimize the reaction conditions for the preparation of keto acetate 4 by using other oxidants and solvents resulted in no improvement. The fact that (-)-bornyl acetate is inexpensive and the observed high yields and excellent enantioselectivities in the Rh-catalyzed 1,4-addition reaction eliminate concerns over the failure of attempts to improve the yield by optimizing the conditions.