Catalytic asymmetric conjugate addition/oxidative dearomatization towards multifunctional spirocyclic compounds

Angewandte Chemie - International Edition

Volumn 50, Issue 26, 2011, Pages 5834-5838

  Rudolph, Alena ^a   Bos, Pieter H ^a   Meetsma, Auke ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

asymmetric catalysis; conjugate addition; dearomatization; oxidation; spiro compounds

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC CONJUGATE ADDITION; CARBON-CARBON BOND; CONJUGATE ADDITION; CYCLOHEXENONES; DEAROMATIZATION; MOLECULAR COMPLEXITY; ONE POT; OXIDATIVE COUPLINGS; SPIRO COMPOUNDS; STEREOCENTERS; UNSATURATED ESTERS;

KETONES; PHENOLS;

CATALYSIS;

EID: 79959242875     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201102069     Document Type: Article

References (81)

1. S. R. Harutyunyan, T. den Hartog, K. Geurts, A. J. Minnaard, B. L. Feringa, Chem. Rev. 2008, 108, 2824-2852
2. A. Alexakis, J. E. Bäckvall, N. Krause, O. PÃmies, M. Diéguez, Chem. Rev. 2008, 108, 2796-2823.
3. H.-C. Guo, J.-A. Ma, Angew. Chem. 2006, 118, 362-375
4. Angew. Chem. Int. Ed. 2006, 45, 354-366
5. T. Jerphagnon, M. G. Pizzuti, A. J. Minnaard, B. L. Feringa, Chem. Soc. Rev. 2009, 38, 1039-1075
6. D. Stolz, U. Kazmaier, Metal Enolates as Synthons in Organic Chemistry in Chemistry of Metal Enolates, Wiley, Chichester, 2009, pp. 355-409.
7. For an example of our studies in this area, see
8. G. P. Howell, S. P. Fletcher, K. Geurts, B. ter Horst, B. L. Feringa, J. Am. Chem. Soc. 2006, 128, 14977-14985; for other selected examples, see
9. K. Oisaki, D. Zhao, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 7439-7443
10. T. Arai, N. Yokoyama, Angew. Chem. 2008, 120, 5067-5070
11. Angew. Chem. Int. Ed. 2008, 47, 4989-4992
12. S. Guo, Y. Xie, X. Hu, C. Xia, H. Huang, Angew. Chem. 2010, 122, 2788-2791
13. Angew. Chem. Int. Ed. 2010, 49, 2728-2731
14. M. Welker, S. Woodward, A. Alexakis, Org. Lett. 2010, 12, 576-579.
15. A. Pelter, S. M. A. Elgendy, J. Chem. Soc. Perkin Trans. 1 1993, 1891-1896; for a review, see
16. S. Quideau, L. Pouységu, D. Deffieux, Synlett 2008, 467-495.
17. For selected reviews, see
18. A. I. Scott, Q. Rev. Chem. Soc. 1965, 19, 1-35
19. D. H. R. Barton, Chem. Ber. 1967, 100, 330-337
20. T. Kametani, K. Fukumoto, Synthesis 1972, 657-674
21. D. H. R. Barton, Half a Century of Free Radical Chemistry, Cambridge University Press, New York, 1993, pp. 7-20.
22. For examples of oxidative dearomatization processes in natural product synthesis, see
23. G. Scheffler, H. Seike, E. J. Sorensen, Angew. Chem. 2000, 112, 4783-4785
24. Angew. Chem. Int. Ed. 2000, 39, 4593-4596
25. J. Zhu, J. A. Porco, Jr., Org. Lett. 2006, 8, 5169-5171
26. A. Bérubé, I. Drutu, J. L. Wood, Org. Lett. 2006, 8, 5421-5424
27. L. H. Mejorado, T. R. R. Pettus, J. Am. Chem. Soc. 2006, 128, 15625-15631
28. S. P. Cook, A. Polara, S. J. Danishefsky, J. Am. Chem. Soc. 2006, 128, 16440-16441
29. J. Gagnepain, F. Castet, S. Quideau, Angew. Chem. 2007, 119, 1555-1557
30. Angew. Chem. Int. Ed. 2007, 46, 1533-1535.
31. N. T. Vo, R. D. M. Pace, F. O'Hara, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 404-405.
32. K. L. Jensen, P. T. Franke, L. T. Nielsen, K. Daasbjerg, K. A. JÃrgensen, Angew. Chem. 2010, 122, 133-137
33. Angew. Chem. Int. Ed. 2010, 49, 129-133.
34. S. L. Schreiber, Science 2000, 287, 1964-1969
35. S. L. Schreiber, Nature 2009, 457, 153-154.
36. D. Magdziak, S. J. Meek, T. R. R. Pettus, Chem. Rev. 2004, 104, 1383-1430.
37. E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415
38. Angew. Chem. Int. Ed. 1998, 37, 388-401
39. M. Sannigrahi, Tetrahedron 1999, 55, 9007-9071
40. R. Pradhan, M. Patra, A. K. Behera, B. K. Mishra, R. K. Behera, Tetrahedron 2006, 62, 779-828
41. S. Kotha, A. C. Deb, K. Lahiri, E. Manivannan, Synthesis 2009, 165-193.
42. L. H. Pettus, R. W. Van De Water, T. R. R. Pettus, Org. Lett. 2001, 3, 905-908
43. L. H. Mejorado, C. Hoarau, T. R. R. Pettus, Org. Lett. 2004, 6, 1535-1538
44. J. Zhu, N. P. Grigoriadis, J. P. Lee, J. A. Porco, Jr, J. Am. Chem. Soc. 2005, 127, 9342-9343
45. reference [6d]
46. J. Qi, J. A. Porco, Jr, J. Am. Chem. Soc. 2007, 129, 12682-12683
47. T. Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka, S. B. Caemmerer, Y. Kita, Angew. Chem. 2008, 120, 3847-3850
48. Angew. Chem. Int. Ed. 2008, 47, 3787-3790
49. reference [7]
50. S. Dong, J. Zhu, J. A. Porco, Jr, J. Am. Chem. Soc. 2008, 130, 2738-2739
51. reference [8]
52. M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. 2010, 122, 2221-2223
53. Angew. Chem. Int. Ed. 2010, 49, 2175-2177.
54. II, see
55. P. S. Baran, J. M. Richter, J. Am. Chem. Soc. 2004, 126, 7450-7451
56. P. S. Baran, J. M. Richter, D. W. Lin, Angew. Chem. 2005, 117, 615-618
57. Angew. Chem. Int. Ed. 2005, 44, 609-612
58. P. S. Baran, M. P. DeMartino, Angew. Chem. 2006, 118, 7241-7244
59. Angew. Chem. Int. Ed. 2006, 45, 7083-7086
60. M. P. DeMartino, K. Chen, P. S. Baran, J. Am. Chem. Soc. 2008, 130, 11546-11560; for a catalytic asymmetric conjugate addition/oxidative coupling sequence of enolates, see
61. M. D. Clift, R. J. Thomson, J. Am. Chem. Soc. 2009, 131, 14579-14583.
62. S.-Y. Wang, S.-J. Ji, T.-P. Loh, J. Am. Chem. Soc. 2007, 129, 276-277
63. S.-Y. Wang, T.-K. Lum, S.-J. Ji, T.-P. Loh, Adv. Synth. Catal. 2008, 350, 673-677
64. S.-Y. Wang, T.-P. Loh, Chem. Commun. 2010, 46, 8694-8703.
65. F. Lõpez, S. R. Harutyunyan, A. Meetsma, A. J. Minnaard, B. L. Feringa, Angew. Chem. 2005, 117, 2812-2816
66. Angew. Chem. Int. Ed. 2005, 44, 2752-2756.
67. A comparison of structure vs. ee achieved during the conjugate addition revealed that for both naphthol and phenol substrates, the proximity of the hydroxy moiety to the α,β-unsaturated ester unit has an impact on the attainable level of enantioselectivity. See the Supporting Information for details.
68. II, see
69. B. Feringa, H. Wynberg, Tetrahedron Lett. 1977, 18, 4447-4450
70. B. Feringa, H. Wynberg, Bioorg. Chem. 1978, 7, 397-408.
71. The conjugate addition of MeMgBr to α,β-unsaturated esters requires specific reaction conditions to proceed in high yield and ee. See reference [14b].
72. A by-product of compound 12, where 1,2-addition of PhMgBr has occurred on the ethyl ester moiety to afford the aryl ketone, accounts for an additional 16% of the reaction mixture.
73. P. Wipf, Y. Kim, H. Jahn, Synthesis 1995, 1549-1561
74. reference [12d]
75. the development of a novel highly selective catalytic oxidative dearomatization process, in particular for phenols, is ongoing.
76. 1-Naphthol substrate 21 with the pendant α,β-unsaturated ester in the 4-position, only afforded trace amounts of the desired product despite numerous attempts at its isolation. See the Supporting Information for substrate synthesis.
77. CCDC 816689 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
78. J. Roithová, P. Milko, J. Am. Chem. Soc. 2010, 132, 281-288.
79. B. K. Trivedi, A. Holmes, T. S. Purchase, A. D. Essenburg, K. L. Hamelehle, B. R. Krause, M. K. Shaw Hes, R. L. Stanfield, Bioorg. Med. Chem. Lett. 1995, 5, 2229-2234.
80. J. R. Allen, K. Biswas, M. C. Bryan, R. Burli, G.-Q. Cao, M. J. Frohn, J. E. Golden, S. Mercede, S. Neira, T. Peterkin, A. J. Pickrell, A. Reed, C. M. Tegley, X. Wang, WO 2008/076427A2, 2008.
81. Z. Xiao, N. Zhang, Y. Lin, G. B. Jones, I. H. Goldberg, Chem. Commun. 2006, 4431-4433.