Influencing the balance between ipso and ω nucleophile addition to (1-arylcyclohexadienyl)iron intermediates in alkaloid synthesis

European Journal of Organic Chemistry

Volumn , Issue 25, 2012, Pages 4716-4732

  Stephenson, G Richard ^a   Anson, Christopher E ^a,b   Malkov, Andrei V ^a,c   Roe, Caroline ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^c LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

Alkaloids; Arene ligands; Iron; Natural products; Regioselectivity; Synthesis design

Indexed keywords

EID: 84865326342     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201200687     Document Type: Article

References (120)

1. For a general discussion of multihapto electrophiles, see:, G. R. Stephenson, in Handbook of Functionalised Organometallics (Eds.:, P. Knochel), Wiley-VCH, Weinheim, Germany, 2005, pp. 569-626.
2. A. J. Pearson, E. H. Kim, H. Sun, Tetrahedron 2010, 66, 4943-4946.
3. K. E. Knott, S. Auschill, A. Jäger, H.-J. Knölker, Chem. Commun. 2009, 1467-1469.
4. R. Czerwonka, K. R. Reddy, E. Baum, H.-J. Knölker, Chem. Commun. 2006, 711-713.
5. K. K. Gruner, T. Hopfmann, K. Matsumoti, A. Jäger, T. Katsuki, H.-J. Knölker, Org. Biomol. Chem. 2011, 9, 2057-2061.
6. O. Kataeva, M. P. Krahl, H.-J. Knölker, Org. Biomol. Chem. 2005, 3, 3099-3101.
7. H.-J. Knölker, T. Hopfmann, Tetrahedron 2002, 58, 8937-8945.
8. W. Fröhner, K. R. Reddy, H.-J. Knölker, Heterocycles 2007, 74, 895-912.
9. A. J. Pearson, X. Fang, J. Org. Chem. 1997, 62, 5284-5292.
10. Y. Zhang, L. S. Liebeskind, J. Am. Chem. Soc. 2006, 128, 465-472.
11. Y. Zhang, L. S. Liebeskind, J. Am. Chem. Soc. 2005, 127, 11258-11259.
12. A. Netz, K. Polborn, H. Nýth, T. T. J. Miller, Eur. J. Org. Chem. 2005, 1823-1833.
13. A. J. Pearson, H. Paramahamsan, J. D. Dudones, Org. Lett. 2004, 6, 2121-2124.
14. T. Watanabe, Y. Tanaka, R. Shoda, R. Sakamoto, K. Kamikawa, M. J. Uemura, J. Org. Chem. 2004, 69, 4152-4158.
15. E. P. Kundig, R. Cannas, M. Laxmisha, L. Ronggang, S. Tchertchian, J. Am. Chem. Soc. 2003, 125, 5642-5643.
16. K. Kamikawa, T. Sakamoto, Y. Tanaka, M. J. Uemura, J. Org. Chem. 2003, 68, 9356-9363. For recent examples by using organoiron complexes, see
17. G. R. Stephenson, C. E. Anson, G. J. Swinson, Tetrahedron Lett. 2011, 52, 3547-3550.
18. A. M. Balfe, D. L. Hughes, R. D. Kelsey, G. R. Stephenson, Tetrahedron Lett. 2010, 51, 6806-6809. Pearson's work on terpene synthesis with opposed Me and OMe groups established the success of this strategy
19. A. J. Pearson, T. R. Perrior, J. Organomet. Chem. 1985, 285, 253-265.
20. A. J. Pearson, P. Ham, J. Chem. Soc. Perkin Trans. 1 1983, 1421-1425.
21. A. J. Pearson, P. Ham, D. C. Rees, J. Chem. Soc. Perkin Trans. 1 1982, 489-497.
22. C. Tao, W. A. Donaldson, J. Org. Chem. 1993, 58, 2134-2143. We used a similar approach towards the terpenes tridachione and bilobanone
23. R. P. Alexander, C. Morley, G. R. Stephenson, J. Chem. Soc. Perkin Trans. 1 1988, 2069-2074.
24. G. R. Stephenson, J. Chem. Soc. Perkin Trans. 1 1982, 2449-2456.
25. R. P. Alexander, T. D. James, G. R. Stephenson, J. Chem. Soc., Dalton Trans. 1987, 2013-2016. For early work towards prostaglandin analogues, see
26. 7. For a survey of organoiron complexes, see
27. G. R. Stephenson, "Organometallic Complexes of Iron" in "Science of Synthesis", Houben-Weyl Methods of Molecular Transformations, vol. 1 (Ed.:, M. Lautens), Georg Thieme Verlag, Stuttgart, 2001, pp. 745-886. For earlier reviews of the applications of the (cyclohexadienyl)iron series, see
28. H.-J. Knölker, A. Braier, D. J. Brocher, S. Cammerer, W. Fröhner, P. Gonser, H. Hermann, D. Herzberg, K. R. Reddy, G. Rohde, Pure Appl. Chem. 2001, 73, 1075-1086.
29. H.-J. Knölker, Chem. Soc. Rev. 1999, 28, 151-157.
30. W. A. Donaldson, Aldrichim. Acta 1997, 30, 17-24.
31. [3,4,14-16,19,20]
32. D. A. Owen, A. V. Malkov, I. M. Palotai, C. Roe, E. J. Sandoe, G. R. Stephenson, Chem. Eur. J. 2007, 13, 4293-4311.
33. C. E. Anson, A. V. Malkov, C. Roe, E. J. Sandoe, G. R. Stephenson, Eur. J. Org. Chem. 2008, 196-213.
34. G. R. Stephenson, S. T. Astley, I. M. Palotai, P. W. Howard, D. A. Owen, S. Williams, in Organic Synthesis via Organometallics (Eds.:, K. H. Dötz, R. W. Hoffmann), Vieweg, Braunschweig, 1991, pp. 169-185. For the concept of "synthetic equivalents to spatially directed organic cations", see
35. A. J. Birch, G. R. Stephenson, Tetrahedron Lett. 1981, 22, 779-782. All the examples in this paper are in the racemic series, but for examples of our work on enantiopure complexes, see
36. G. R. Stephenson, Aust. J. Chem. 1981, 34, 2339-2345.
37. P. W. Howard, G. R. Stephenson, S. C. Taylor, J. Organomet. Chem. 1989, 370, 97-109.
38. P. W. Howard, G. R. Stephenson, S. C. Taylor, J. Chem. Soc., Chem. Commun. 1990, 1182-1184.
39. G. R. Stephenson, P. W. Howard, S. C. Taylor, J. Chem. Soc., Chem. Commun. 1991, 127-129.
40. M. A. Khan, M. F. Mahon, A. J., W. Stewart, S. E. Lewis, Organometallics 2012, 29, 199-204.
41. M. J. Palframan, G. Kociok-Köhn, S. E. Lewis, Org. Lett. 2011, 13, 3150-3153.
42. S. Pilgrim, G. Kociok-Köhn, M. D. Lloyd, S. E. Lewis, Chem. Commun. 2011, 47, 4799-4801.
43. J. A. Griffen, A. M. le Coz, G. Kociok-Köhn, M. A. Khan, A. J. W. Stewart, S. E. Lewis, Org. Biomol. Chem. 2011, 9, 3920-3928.
44. M. A. Khan, J. P. Lowe, A. L. Johnson, A. J. W. Stewart, S. E. Lewis, Chem. Commun. 2011, 47, 215-217.
45. D. van der Waals, T. Pugh, M. A. Khan, A. J. W. Stewart, A. L. Johnson, S. E. Lewis, Chem. Central J. 2011, 5, 80.
46. [2p] Absolute configurations
47. A. J. Birch, W. D. Raverty, G. R. Stephenson, J. Chem. Soc., Chem. Commun. 1980, 857-859.
48. [8a]
49. The "potential symmetry plane" of the complex lies through C3 and C6 of the dienyl ligand. Unsymmetrically placed substituents, which are needed for the complex to be chiral, differentiate the sides of this central plane. See: G. R. Stephenson (Ed.), Advanced Asymmetric Synthesis Chapman and Hall, London, 1996, pp. 315-316.
50. R. D. A. Hudson, C. E. Anson, M. F. Mahon, G. R. Stephenson, J. Organomet. Chem. 2001, 630, 88-103.
51. C. E. Anson, R. D. A. Hudson, D. G. Smyth, G. R. Stephenson, Appl. Organomet. Chem. 2001, 15, 16-22.
52. E. van den Beuken, S. Samson, E. J. Sandoe, G. R. Stephenson, J. Organomet. Chem. 1997, 530, 251-253.
53. R. D. A. Hudson, S. A. Osborne, G. R. Stephenson, Tetrahedron 1997, 53, 4095-4104.
54. R. D. A. Hudson, S. A. Osborne, G. R. Stephenson, Tetrahedron Lett. 1996, 37, 9009-9012.
55. J. A. S. Howell, A. G. Bell, P. J. O'Leary, G. R. Stephenson, M. Hastings, P. W. Howard, D. A. Owen, A. J. Whitehead, P. McArdle, D. Cunningham, Organometallics 1996, 15, 4247-4257.
56. A. V. Malkov, G. R. Stephenson, J. Organomet. Chem. 1995, 489, C44-C47.
57. G. R. Stephenson, K. Milne, Aust. J. Chem. 1994, 47, 1605-1654.
58. S. T. Astley, G. R. Stephenson, Synlett 1992, 507-509.
59. M. J. Dunn, R. F. W. Jackson, G. R. Stephenson, Synlett 1992, 905-906.
60. G. R. Stephenson, P. W. Howard, S. C. Taylor, J. Organomet. Chem. 1991, 419, C14-C17.
61. G. R. Stephenson, P. W. Howard, D. A. Owen, A. J. Whitehead, J. Chem. Soc., Chem. Commun. 1991, 641-642.
62. D. A. Owen, G. R. Stephenson, H. Finch, S. Swanson, Tetrahedron Lett. 1990, 31, 3401-3404.
63. G. R. Stephenson, M. Voyle, S. Williams, Tetrahedron Lett. 1990, 31, 3979-3982.
64. D. A. Owen, G. R. Stephenson, H. Finch, S. Swanson, Tetrahedron Lett. 1989, 30, 2607-2610.
65. I. M. Palotai, G. R. Stephenson, W. J. Ross, D. E. Tupper, J. Organomet. Chem. 1989, 364, C11-C14.
66. I. M. Palotai, G. R. Stephenson, L. A. P. Kane-Maguire, J. Organomet. Chem. 1987, 319, C5-C10.
67. R. P. Alexander, G. R. Stephenson, J. Chem. Soc., Dalton Trans. 1987, 885-888.
68. G. R. Stephenson, J. Chem. Soc. Perkin Trans. 1 1982, 2449-2456.
69. G. R. Stephenson, H. Finch, D. A. Owen, S. Swanson, Tetrahedron 1993, 49, 5649-5662.
70. E. J. Sandoe, G. R. Stephenson, S. Swanson, Tetrahedron Lett. 1996, 37, 6283-6286.
71. G. R. Stephenson, D. A. Owen, H. Finch, S. Swanson, Tetrahedron Lett. 1991, 32, 1291-1244.
72. Part of this work has been the subject of a preliminary communication:, C. Roe, E. J. Sandoe, G. R. Stephenson, C. E. Anson, Tetrahedron Lett. 2008, 49, 650-653.
73. C. Roe, E. J. Sandoe, G. R. Stephenson, Eur. J. Org. Chem. 2011, 1664-1681.
74. C. Roe, G. R. Stephenson, Org. Lett. 2008, 10, 189-192.
75. L. Yang, X. Wang, Z. Pan, M. Zhou, W. Chen, X. Yang, Synlett 2011, 207-210.
76. J. McNulty, J. J. Nair, J. R. L. Little, J. D. Brennan, J. Bastida, Bioorg. Med. Chem. Lett. 2010, 20, 5290-5294.
77. K. M. Bogle, D. J. Hirst, D. J. Dixon, Tetrahedron 2010, 66, 6399-6410.
78. J. Collins, U. Rinner, M. Moser, T. Hudlicky, I. Ghiviriga, A. E. Romero, A. Kornienko, D. Ma, C. Griffin, S. Pandey, J. Org. Chem. 2010, 75, 3069-3084.
79. G. Szanto, L. Hegedus, L. Mattyasovszko, A. Simon, I. Bitter, G. Toth, L. Toke, I. Kadas, Tetrahedron 2009, 65, 8412-8417.
80. K. C. Guerard, C. Sabot, L. Racicot, S. Canesi, J. Org. Chem. 2009, 74, 2039-2045.
81. A.-W. Hong, T.-H. Cheng, V. Raghukumar, C.-K. Sha, J. Org. Chem. 2008, 73, 7580-7585.
82. T. Dohl, Y. Minamitsuji, A. Maruyama, S. Hirose, Y. Kita, Org. Lett. 2008, 10, 3559-3562.
83. A. Pulpapka, S. C. Bergmeier, Synthesis 2008, 1420-1430. Reviews
84. J. Zhong, Nat. Prod. Rep. 2011, 28, 1126-1142.
85. A. Kornieko, A. Evidente, Chem. Rev. 2008, 108, 1982-2014. For synthetic strategies, see also
86. U. Rinner, T. Hudlicky, Synlett 2005, 365-387.
87. 5-cyclohexadienyl)iron series of electrophiles
88. G. R. Stephenson, S. T. Astley, I. M. Palotai, P. W. Howard, D. A. Owen, S. Williams, in Organic Synthesis via Organometallics (Eds.:, K. H. Dötz, R. W. Hoffmann), Vieweg, Braunschweig, Germany, 1991, pp. 169-185. For multiple addition by the iterative approach, see
89. P. W. Howard, G. R. Stephenson, S. C. Taylor, J. Organomet. Chem. 1988, 339, C5-C8.
90. G. R. Stephenson, I. M. Palotai, W. J. Ross, D. E. Tupper, Synlett 1991, 586-588.
91. A. V. Malkov, A. Auffrant, C. Renard, E. Rose, F. Rose-Munch, D. A. Owen, E. J. Sandoe, G. R. Stephenson, Inorg. Chim. Acta 1999, 296, 139-149.
92. C. Roe, E. J. Sandoe, G. R. Stephenson, Tetrahedron Lett. 2010, 51, 591-595.
93. J. L. Charlton, C. J. Oleschuk, G.-L. Chee, J. Org. Chem. 1996, 61, 3452-3457.
94. B. A. Keay, H. P. Plauman, D. Rajapaksa, R. Rodrigo, Canad. J. Chem. 1983, 61, 1987-1995.
95. K. Matcha, S. Ghost, Tetrahedron Lett. 2010, 51, 6924-6927.
96. G. Pandey, S. Lluckorse, A. Budakoti, V. G. Puranik, Tetrahedron Lett. 2010, 51, 2975-2978.
97. H. Fuji, K. Okada, M. Ishihara, S. Hanamura, Y. Osa, T. Nemoto, H. Nagase, Tetrahedron 2009, 65, 10623-10630.
98. G. I. Feutrill, M. B. Whitelaw, Aust. J. Chem. 1981, 34, 1523-1528.
99. D. A. Owen, G. R. Stephenson, H. Finch, S. Swanson, J. Organomet. Chem. 1990, 395, C5-C8.
100. W. A. Donaldson, M.-J. Jin, P. T. Bell, Organometallics 1993, 12, 1174-1179.
101. W. A. Donaldson, L. Shang, M. Ramaswamy, C. A. Droste, C. Tao, D. W. Bennett, Organometallics 1995, 14, 5119-5126.
102. W. A. Donaldson, L. Shang, C. Tao, Y. K. Yun, M. Ramaswamy, V. G. Young Jr., J. Organomet. Chem. 1997, 539, 87-98.
103. M. A. Hossain, W. A. Donaldson, M.-J. Jin, J. Organomet. Chem. 2001, 630, 5-10.
104. S. Chaudhury, W. A. Donaldson, D. W. Bennett, D. T. Haworth, T. A. Siddiquee, J. M. Kloss, J. Organomet. Chem. 2004, 689, 1437-1443.
105. P. Zandbergen, A. Vandennieuwendijk, J. Brussee, A. Vandergen, Tetrahedron 1992, 48, 3977-3982.
106. Y. Shvo, E. Hazum, J. Chem. Soc., Chem. Commun. 1974, 336-337.
107. For an early example in alkaloid Synthesis see:, A. J. Pearson, Tetrahedron Lett. 1981, 40, 4033-4036.
108. F. Ye, Y. Shi, L. Zhou, Q. Xiao, Y. Zhang, J. Wang, Org. Lett. 2011, 13, 5020-5023.
109. S. Bernhardt, G. Manolikakes, T. Kunz, P. Knochel, Angew. Chem. Int. Ed. 2011, 50, 9205-9209.
110. Y.-L. Zhao, Y. Li, S.-M. Li, Y.-G. Zhou, F.-Y. Sun, L.-X. Gao, F.-S. Fu, Adv. Synth. Catal. 2011, 353, 1543-1550.
111. A. V. Malkov, G. R. Stephenson, J. Organomet. Chem. 1995, 489, C74-C77.
112. 13C NMR spectra of 11 cyclohexadienyliron complexes, see
113. [40]
114. I. A. Rezvukhin, V. N. Piottukh-Peletskii, R. N. Berezina, V. G. Shubin, Izv. Akad. Nauk SSSR, Ser. Khim. 1973, 705-707.
115. C. J. Moody, G. J. Warrellow, J. Chem. Soc. Perkin Trans. 1 1990, 2929-2936.
116. S. P. Khanapure, E. R. Biehl, J. Org. Chem. 1990, 55, 1471-1475.
117. [9]
118. S. P. Chavan, D. A. Khobragade, A. B. Pathak, U. R. Kalkote, Tetrahedron Lett. 2004, 45, 5263-5265.
119. G. M. Sheldrick, Acta Crystallogr., Sect. A 2008, 64, 112-122.
120. P. van der Sluis, A. L. Spek, Acta Crystallogr., Sect. A 1990, 46, 194.