Solvolysis reactions at the 13th carbon of 1-aryl organoiron complexes

Tetrahedron Letters

Volumn 51, Issue 4, 2010, Pages 591-595

  Roe, Caroline ^a   Sandoe, Elizabeth J ^a   Richard Stephenson, G ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

Deprotection; Dihydrofluorene; Electrophilic cyclisation; Organoiron; Solvolysis

Indexed keywords

5AALPHA CYANOMETHYL 5A,8A DIHYDROFLUORENE TRICARBONYLIRON COMPLEX; ALKALOID DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; CARBON; IRON COMPLEX; TRICARBONYLIRON; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; SOLVOLYSIS; SYNTHESIS;

EID: 72149085710     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.052     Document Type: Article

References (76)

1. Owen D.A., Malkov A.V., Palotai I.M., Roe C., Sandoe E.J., and Stephenson G.R. Chem. Eur. J. 13 (2007) 4293-4311
2. Anson C.E., Malkov A.V., Roe C., Sandoe E.J., and Stephenson G.R. Eur. J. Org. Chem. (2008) 196-213
3. Roe C., and Stephenson G.R. Org. Lett. 10 (2008) 189-192
4. Roe C., Sandoe E.J., Stephenson G.R., and Anson C.E. Tetrahedron Lett. 49 (2008) 650-653
5. Malkov A.V., Auffrant A., Renard C., Rose E., Rose-Munch F., Owen D.A., Sandoe E.J., and Stephenson G.R. Inorg. Chim. Acta 296 (1999) 139-149
6. Stephenson G.R. Organometallic Complexes of Iron. In: Lautens M. (Ed). Science of Synthesis; Houben-Weyl Methods of Molecular Transformations: Vol. 1 Complexes with transition metal-carbon π-bonds and compounds of groups 10-8 (Ni, Pd, Pt, CO, Rh, Ir, Fe, Ru, Os) (2001), Georg Theime, Stuttgart 745-886
7. For other examples in alkaloid synthesis, see:. Pearson A.J., and Wang X. Tetrahedron Lett. 46 (2005) 4809-4811
8. Knölker H.-J., Baum E., and Kosub M. Synlett (2004) 1769-1771
9. Danks T.N., and Wagner G. J. Organomet. Chem. 689 (2004) 2543-2557
10. Chaudhury S., Donaldson W.A., Bennett D.W., Haworth D.T., Siddiquee T.A., and Kloss J.M. J. Organomet. Chem. 689 (2004) 1437-1443
11. Schobert R., Mangold A., Baumann T., Milius W., and Hampel F. J. Organomet. Chem. 689 (2004) 575-584
12. Fairlamb I.J.S., Syvaenne S.M., and Whitwood A.C. Synlett (2003) 1693-1697
13. Geoffroy P., Gassmann D., Cenac C., and Franck-Neumann M. J. Organomet. Chem. 678 (2003) 68-71
14. Knölker H.-J., Baum E., and Hopfmann T. Tetrahedron 55 (1999) 10391-10412
15. Knölker H.-J., and Wolpert M. Tetrahedron Lett. 38 (1997) 533-536
16. Lesma G., Palmisano G., and Tollari S. J. Chem. Soc., Perkin Trans. 1 (1984) 1593-1597
17. Pearson A.J., and Rees D.C. J. Am. Chem. Soc. 104 (1982) 1118-1119
18. Pearson A.J. Tetrahedron Lett. 22 (1981) 4033-4036
19. for other target molecule classes, see:. Dunn M.J., Jackson R.W.F., and Stephenson G.R. Synlett (1992) 905-906
20. Stephenson G.R., Thomas R.D., and Cassidy F. Synlett (1992) 247-248
21. Knölker H.-J., and Hartmann K. Synlett (1991) 428-430
22. Alexander R.P., Morley C., and Stephenson G.R. J. Chem. Soc., Perkin Trans. 1 (1988) 2069-2074
23. Birch A.J., Kelly L.F., and Weerasuria D.V. J. Org. Chem. 53 (1988) 278-281
24. Pearson A.J., and Chen Y.-S. J. Org. Chem. 51 (1986) 1939-1947
25. Bandara B.M.R., Birch A.J., and Kelly L.F. J. Org. Chem. 49 (1984) 2496
26. Pearson A.J., Haywood G.C., and Chandler M. J. Chem. Soc., Perkin Trans. 1 (1982) 2631-2639
27. Stephenson G.R. J. Chem. Soc., Perkin Trans. 1 (1982) 2449-2456
28. Recent examples of organoiron methodology:. Christie S.D.R., Cummins J., Elsegood M.R.J., and Dawson G. Synlett (2009) 257-259
29. Williams I., Reeves K., Kariuki B.M., and Cox L.R. Org. Biomol. Chem. 5 (2007) 3325-3329
30. Emme I., Labahn T., and De Meijere A. Eur. J. Org. Chem. (2006) 399-404
31. Seigal B.A., An M.H., and Snapper M.L. Angew. Chem., Int. Ed. 44 (2005) 4929-4932
32. For other recent synthetic approaches, see:. Szanto G., Hegedus L., Mattyasovszky L., Simon A., Simon A., Bitter I., Toth G., Toke L., and Kadas I. Tetrahedron 65 (2009) 8412-8417
33. Guerard K.C., Sabot C., Racicot L., and Canesi S. J. Org. Chem. 74 (2009) 2039-2045
34. Hong A.-W., Cheng T.-H., Raghukumar V., and Sha C.-K. J. Org. Chem. 73 (2008) 7580-7585
35. Matveenko M., Kokas O.J., Banwell M.G., and Willis A.C. Org. Lett. 9 (2007) 3683-3685
36. Bohno M., Sugie K., Imase H., Yusof Y.B., Oishi T., and Chida N. Tetrahedron 63 (2007) 6977-6989
37. Zhang F.M., Tu Y.-Q., Liu J.-D., Fan X.-H., Shi L., Hu X.-D., Wang S.-H., and Zhang Y.-Q. Tetrahedron 62 (2006) 9446-9455
38. Trost B.M., Tang W., and Toste F.D. J. Am. Chem. Soc. 127 (2005) 14785-14803
39. Kodama S., Takita H., Kajimoto T., Nishide K., and Node M. Tetrahedron 60 (2004) 4901-4907 for the example in Figure 1, see Ref. 9
40. Pereira J., Barlier M., and Guillou C. Org. Lett. 9 (2007) 3101-3103
41. Youn S.W. Org. Prep. Proced. Int. 38 (2006) 505-591
42. Czerwinska A.G., and Cook J.M. Adv. Heterocycl. Nat. Prod. Synth. 3 (1996) 217-277
43. Cox E.D., and Cook J.M. Chem. Rev. 95 (1995) 1797-1842
44. For recent examples of the use of the Pictet-Spengler reaction in alkaloid synthesis, see:. Godecke T., Lankin D.C., Nikolic D., Chen S.-N., van Breemen R.B., Farnsworth N.R., and Pauli G.F. Org. Lett. 11 (2009) 1143-1146
45. Agarwal P.K., Sharma S.K., Sawant D., and Kundu B. Tetrahedron 65 (2009) 1153-1161
46. Wu Y.-C., Liron M., and Zhu J. J. Am. Chem. Soc. 130 (2008) 7148-7152
47. For an example employing organoiron complexes, see:. Pearson A.J., Ham P., Ong C.W., Perrior T.R., and Rees D.C. J. Chem. Soc., Perkin Trans. 1 (1982) 1527-1534
48. Stephenson G.R. Polyfunctional Electrophilic Multihapto-organometallics for Organic Synthesis. In: Knochel P. (Ed). Handbook of Functionalised Organometallics (2005), Wiley-VCH, Weinheim 569-626
49. This nomenclature has recently been discussed in detail; see Ref. 11, pp 573-574.
50. Owen D.A., Stephenson G.R., Finch H., and Swanson S. Tetrahedron Lett. 31 (1990) 3401-3404
51. Stephenson G.R., Owen D.A., Finch H., and Swanson S. Tetrahedron Lett. 32 (1991) 1291-1294
52. Astley S.T., and Stephenson G.R. Synlett (1992) 507-509
53. Stephenson G.R., Finch H., Owen D.A., and Swanson S. Tetrahedron 49 (1993) 5649-5662
54. McKillop A., Stephenson G.R., and Tinlk M. J. Chem. Soc., Perkin Trans. 1 (1993) 1827-1828
55. Howell J.A.S., Bell A.G., O'Leary P.J., Stephenson G.R., Hastings M., Howard P.W., Owen D.A., Whitehead A.J., McArdle P., and Cunningham D. Organometallics 15 (1996) 4247-4257
56. Hudson R.D.A., Osborne S.A., and Stephenson G.R. Tetrahedron 53 (1997) 4095-4104
57. Tranchier J.P., Chavignon R., Prim D., Aufrant A., Giner Planas J., Rose-Munch F., Rose E., and Stephenson G.R. Tetrahedron Lett. 42 (2001) 3311-3313
58. Simpkins, S. M. E. Ph.D. Thesis, University of East Anglia, 2001.
59. Peters K.S. Chem. Rev. 107 (2007) 859-873
60. Birch A.J., Cross P.E., Lewis J., White D.A., and Wild S.B. J. Chem. Soc. A (1968) 332-340
61. Owen D.A., Stephenson G.R., Finch H., and Swanson S. Tetrahedron Lett. 30 (1989) 2607-2610
62. For eamples with other highly functionalised diarylcuprates, see:. McKillop A., Stephenson G.R., and Tinkl M. Synlett (1995) 669-670
63. Charlton J.L., and Alauddin M.M. J. Org. Chem. 51 (1986) 3490-3493
64. Sarma J.C., Borbaruah M., Sarma D.N., Batua N.C., and Sharma R.P. Tetrahedron 42 (1986) 3999-4006
65. Collet A., and Gabard J. J. Org. Chem. 45 (1980) 5400-5401
66. Lindsey A.S. J. Chem. Soc. (1965) 1685-1692
67. White J.D., and Gesner B.D. Tetrahedron 30 (1974) 2273-2277
68. Barbour L.J., Steed J.W., and Atwood J.L. J. Chem. Soc., Perkin Trans. 2 (1995) 857-860
69. Chandler M., Parsons P.J., and Mincione E. Tetrahedron Lett. 24 (1983) 5781-5784
70. Lipshutz B.H., and Millar T.A. Tetrahedron Lett. 30 (1989) 7149-7152
71. Sandoe E.J., Stephenson G.R., and Swanson S. Tetrahedron Lett. 37 (1996) 6283-6286
72. Sandoe, E. J. PhD Thesis, University of East Anglia, Norwich, 1996.
73. 6: C, 57.7; H, 4.4, N, 3.2. Found: C, 57.7; H, 4.2; N, 3.0.
74. 2 to give the alcohol 13 which was shown to be different (TLC) from the product 18.
75. Franck-Neumann M., Sedrati M., and Mokhi M. New J. Chem. 14 (1990) 471-480
76. Rivera A.V., and Sheldrick G.M. Acta Crystallogr., Sect. B B34 (1978) 1716-1718