Formal ring-opening/cross-coupling reactions of 2-pyrones: Iron-catalyzed entry into stereodefined dienyl carboxylates

Angewandte Chemie - International Edition

Volumn 52, Issue 49, 2013, Pages 13071-13075

  Sun, Chang Liang ^a   Fürstner, Alois ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

cross coupling; dienes; heterocycles; iron; natural products

Indexed keywords

ACETYLACETONATES; CROSS-COUPLINGS; DIENES; HETEROCYCLES; INTEGRAL PART; IRON CATALYSIS; LEAVING GROUPS; NATURAL PRODUCTS;

CARBOXYLATION; CATALYSIS; CHEMICAL BONDS; OLEFINS; SCAFFOLDS;

IRON;

EID: 84888600992     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201307028     Document Type: Article

References (82)

1. B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500-1511.
2. E. Nakamura, N. Yoshikai, J. Org. Chem. 2010, 75, 6061-6067.
3. T. Hatakeyama, K. Ishizuka, M. Nakamura, J. Synth. Org. Chem. Jpn. 2011, 69, 1282-1298.
4. G. Cahiez, H. Avedissian, Synthesis 1998, 1199-1205.
5. E. B. Bauer, Curr. Org. Chem. 2008, 12, 1341-1369.
6. W. M. Czaplik, M. Mayer, J. Cvengroš, A. Jacobi von Wangelin, ChemSusChem 2009, 2, 396-417.
7. K. Gopalaiah, Chem. Rev. 2013, 113, 3248-3296.
8. A. Fürstner, R. Martin, Chem. Lett. 2005, 34, 624-629.
9. C. Risatti, K. J. Natalie, Jr., Z. Shi, D. A. Conlon, Org. Process Res. Dev. 2013, 17, 257-264
10. A. Fürstner, A. Leitner, G. Seidel, Org. Synth. 2005, 81, 33-41.
11. A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856-13863
12. A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632-635
13. Angew. Chem. Int. Ed. 2002, 41, 609-612.
14. A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323
15. Angew. Chem. Int. Ed. 2003, 42, 308-311
16. B. Scheiper, F. Glorius, A. Leitner, A. Fürstner, Proc. Natl. Acad. Sci. USA 2004, 101, 11960-11965.
17. B. Scheiper, M. Bonnekessel, H. Krause, A. Fürstner, J. Org. Chem. 2004, 69, 3943-3949
18. G. Seidel, D. Laurich, A. Fürstner, J. Org. Chem. 2004, 69, 3950-3952
19. A. Fürstner, P. Hannen, Chem. Eur. J. 2006, 12, 3006-3019
20. A. Fürstner, A. Schlecker, Chem. Eur. J. 2008, 14, 9181-9191.
21. For representative studies, see A. L. Silberstein, S. D. Ramgren, N. K. Garg, Org. Lett. 2012, 14, 3796-3799
22. T. Mesganaw, N. K. Garg, Org. Process Res. Dev. 2013, 17, 29-39
23. T. Agarwal, S. P. Cook, Org. Lett. 2013, 15, 96-99
24. O. M. Kuzmina, A. K. Steib, D. Flubacher, P. Knochel, Org. Lett. 2012, 14, 4818-4821
25. M. C. Perry, A. N. Gillett, T. C. Law, Tetrahedron Lett. 2012, 53, 4436-4439
26. G. Cahiez, O. Gager, J. Buendia, C. Patinote, Chem. Eur. J. 2012, 18, 5860-5863
27. R. K. Shiroodi, A. S. Dudnik, V. Gevorgyan, J. Am. Chem. Soc. 2012, 134, 6928-6931
28. S. Gülak, A. Jacobi von Wangelin, Angew. Chem. 2012, 124, 1386-1390
29. Angew. Chem. Int. Ed. 2012, 51, 1357-1361
30. H. Nishikado, H. Nakatsuji, K. Ueno, R. Nagase, Y. Tanabe, Synlett 2010, 2087-2092
31. C. M. Rao Volla, P. Vogel, Angew. Chem. 2008, 120, 1325-1327
32. Angew. Chem. Int. Ed. 2008, 47, 1305-1307
33. B.-J. Li, L. Xu, Z.-H. Wu, B.-T. Guan, C.-L. Sun, B.-Q. Wang, Z.-J. Shi, J. Am. Chem. Soc. 2009, 131, 14656-14657
34. U. S. Larsen, L. Martiny, M. Begtrup, Tetrahedron Lett. 2005, 46, 4261-4263
35. K. Itami, S. Higashi, M. Mineno, J. Yoshida, Org. Lett. 2005, 7, 1219-1222
36. N. Hayashi, M. Nakada, Tetrahedron Lett. 2009, 50, 232-235
37. G. Cahiez, O. Gager, V. Habiak, Synthesis 2008, 2636-2644
38. G. Cahiez, V. Habiak, O. Gager, Org. Lett. 2008, 10, 2389-2392.
39. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev. 2011, 111, 1293-1314.
40. For nickel-catalyzed ring-opening/cross-coupling of cyclic enol ethers, see:, E. Wenkert, E. L. Michelotti, C. S. Swindell, M. Tingoli, J. Org. Chem. 1984, 49, 4894-4899
41. P. J. Kocieński, M. Pritchard, S. N. Wadman, R. J. Whitby, C. L. Yeates, J. Chem. Soc. Perkin Trans. 1 1992, 3419-3429
42. P. A. Ashworth, N. J. Dixon, P. J. Kocieński, S. N. Wadman, J. Chem. Soc. Perkin Trans. 1 1992, 3431-3438
43. for cross-coupling/desulfurization of various sulfur-containing heterocycles, see:, T.-Y. Luh, Z.-J. Ni, Synthesis 1990, 89-103
44. M. Tiecco, M. Tingoli, E. Wenkert, J. Org. Chem. 1985, 50, 3828-3831
45. A. Oviedo, A. Arévalo, M. Flores-Alamo, J. J. Garcia, Organometallics 2012, 31, 4039-4045
46. Y.-H. Cho, A. Kina, T. Shimada, T. Hayashi, J. Org. Chem. 2004, 69, 3811-3823
47. for a ring opening Kumada coupling of cyclic ethers, see:, J. W. Dankwardt, Angew. Chem. 2004, 116, 2482-2486
48. Angew. Chem. Int. Ed. 2004, 43, 2428-2432
49. for formal ring-opening/cross-coupling of cyclic enol ethers by a 1,2-metallate rearrangement, see:, K. Jarowicki, P. J. Kocienski, L. Qun, Org. Synth. 2002, 79, 11-18.
50. M. Furber, J. M. Herbert, R. J. K. Taylor, J. Chem. Soc. Perkin Trans. 1 1989, 683-690
51. B. Feith, H.-M. Weber, G. Maas, Chem. Ber. 1986, 119, 3276-3296
52. T. Fujisawa, Y. Kurita, M. Kawashima, T. Sato, Chem. Lett. 1982, 1641-1642
53. for accounts on heterocycle ring-opening by other nucleophiles, see:, C. D. Vanderwal, J. Org. Chem. 2011, 76, 9555-9567
54. G. Piancatelli, M. D'Auria, F. D'Onofrio, Synthesis 1994, 867-889.
55. 3] are the actual catalyst because copper leads to 1,4-addition of Grignard reagents to 2-pyrones without ring opening, see:, B. Mao, M. Fañanás-Mastral, B. L. Feringa, Org. Lett. 2013, 15, 286-289.
56. F. Frébault, M. T. Oliveira, E. Wöstefeld, N. Maulide, J. Org. Chem. 2010, 75, 7962-7965.
57. T. L. Gilchrist, Heterocyclenchemie, VCH, Weinheim, 1995.
58. For iron-catalyzed C - C bond formation under opening of a strained carbocyclic ring, see:, B. D. Sherry, A. Fürstner, Chem. Commun. 2009, 7116-7118.
59. For a different entry into these motifs starting from pyrones, see:, C. Souris, F. Frébault, A. Patel, D. Audisio, K. N. Houk, N. Maulide, Org. Lett. 2013, 15, 3242-3245.
60. A. Fürstner, K. Majima, R. Martín, H. Krause, E. Kattnig, R. Goddard, C. W. Lehmann, J. Am. Chem. Soc. 2008, 130, 1992-2004.
61. The ready preparation of the substrates used herein illustrates this aspect. For details, see the Supporting Information. For a particularly convenient new entry into 4-hydroxy-2-pyrones, see:, W. Chaładaj, M. Corbet, A. Fürstner, Angew. Chem. 2012, 124, 7035-7039
62. Angew. Chem. Int. Ed. 2012, 51, 6929-6933.
63. P. T. Northcote, J. W. Blunt, M. H. G. Munro, Tetrahedron Lett. 1991, 32, 6411-6414
64. D. Romo, R. M. Rzasa, H. A. Shea, K. Park, J. M. Langenhan, L. Sun, A. Akhiezer, J. O. Liu, J. Am. Chem. Soc. 1998, 120, 12237-12254
65. G. Pattenden, D. J. Critcher, M. Remuiñán, Can. J. Chem. 2004, 82, 353-365.
66. W.-K. Low, Y. Dang, T. Schneider-Poetsch, Z. Shi, N. S. Choi, R. M. Rzasa, H. A. Shea, S. Li, K. Park, G. Ma, D. Romo, J. O. Liu, Methods Enzymol. 2007, 431, 303-324.
67. S. Di Marco, A. Cammas, X. J. Lian, E. N. Kovacs, J. F. Ma, D. T. Hall, R. Mazroui, J. Richardson, J. Pelletier, I. E. Gallouzi, Nat. Commun. 2012, 3, 896.
68. F. Reyes, R. Martín, R. Fernández, J. Nat. Prod. 2006, 69, 668-670.
69. M. F. Semmelhack, in Organometallics in Synthesis. A Manual, 2 nd ed., (Ed.: M. Schlosser,), Wiley, Chichester, pp. 1003-1121.
70. K. Fukuhara, H. Urabe, Tetrahedron Lett. 2005, 46, 603-606
71. S. Okada, K. Arayama, R. Murayama, T. Ishizuka, K. Hara, N. Hirone, T. Hata, H. Urabe, Angew. Chem. 2008, 120, 6966-6970
72. Angew. Chem. Int. Ed. 2008, 47, 6860-6864
73. T. Hata, T. Nakada, Y. T. Oh, N. Hirone, H. Urabe, Adv. Synth. Catal. 2013, 355, 1736-1740.
74. C. H. DePuy, R. L. Parton, T. Jones, J. Am. Chem. Soc. 1977, 99, 4070-4075.
75. A. Fürstner, H. Krause, C. W. Lehmann, Angew. Chem. 2006, 118, 454-458
76. Angew. Chem. Int. Ed. 2006, 45, 440-444.
77. A. Fürstner, R. Martin, H. Krause, G. Seidel, R. Goddard, C. W. Lehmann, J. Am. Chem. Soc. 2008, 130, 8773-8787.
78. For a leading reference see the following and the literature cited therein:, B. Schmidt, O. Kunz, Eur. J. Org. Chem. 2012, 1008-1018.
79. For structural evidence for C-metalated iron ester enolates, see:, P. Laurent, S. Sabo-Etienne, A.-M. Larsonneur, H. des Abbayes, J. Chem. Soc. Chem. Commun. 1988, 929-930
80. for O-metalated iron ketone enolates, see:, S. Sabo-Etienne, H. des Abbayes, L. Toupet, Organometallics 1987, 6, 2262-2263
81. D. Noda, Y. Sunada, T. Hatakeyama, M. Nakamura, H. Nagashima, Chem. Commun. 2012, 48, 12231-12333
82. S. Kiyota, J.-I. Tamuki, N. Komine, M. Hirano, S. Komiya, Chem. Lett. 2005, 34, 498-499.