Intramolecular carbolithiation reactions of aryllithiums in the synthesis of carbocyclic and heterocyclic compounds

Targets in Heterocyclic Systems

Volumn 14, Issue , 2010, Pages 124-149

  Martínez Estíbalez, Unai ^a   Gómez Sanjuán, Asier ^a   García Calvo, Oihane ^a   Arrasate, Sonia ^a   Sotomayor, Nuria ^a   Lete, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85043550288     PISSN: 17249449     EISSN: None     Source Type: Book Series    
DOI: None     Document Type: Article

References (124)

1. Wakefield, B.J. The Chemistry of Organolithium Compounds, 2nd ed., Pergamon Press: New York, 1990.
2. Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon Press: New York, 2002.
3. The Chemistry of Organolithium Compounds; Patai Series: The Chemistry of Functional Groups; Rappoport, Z., Marek, I., Eds., Wiley: Chichester, 2004; Vol. 1.
4. Gribble, G.W. In Science of Synthesis [Houben-Weyl Methods of Molecular Transformations]; Majewski, M., Snieckus, V., Eds., Georg Thieme Verlag: Sttutgart, 2006; Vol. 8a, pp. 357-426.
5. Bailey, W.F., Patricia, J.I. J. Organomet. Chem. 1988, 352, 1-46.
6. Beak, P., Allen, D.J., Lee, W.K. J. Am. Chem. Soc. 1990, 112, 1629-1630.
7. Beak, P., Allen, D.J. J. Am. Chem. Soc. 1992, 114, 3420-3425.
8. Reich, H.J., Green, D.P., Phillips, N.H. J. Am. Chem. Soc. 1991, 113, 1414-1416.
9. Reich, H.J., Gudmundsson, B.O., Green, D.P., Bevan, M.J., Reich, I.L. Helv. Chim. Acta 2002, 85, 3748-3772.
10. Reich, H.J., Bevan, M.J., Gudmundsson, B.O., Puckett, C.L. Angew. Chem. 2002, 41, 3436-3439.
11. Parham, W.E., Bradsher, C.K. Acc. Chem. Res. 1982, 15, 300-305.
12. Gray, M., Tinkl, M., Snieckus, V. In Comprehensive Organometallic Chemistry II; Abel, E.W., Stone, F.G.A., Wilkinson, G., Eds., Pergamon Press: Exeter, 1995; Vol. 11, pp. 66-92.
13. Ardeo, A., Collado, M.I., Osante, I., Ruiz, J., Sotomayor, N., Lete, E. In Targets in Heterocyclic Systems; Attanasi, O.A., Spinelli, D., Eds., Società Chimica Italiana: Rome, 2001; Vol. 5, pp. 393-418.
14. Sotomayor, N., Lete, E. Curr. Org. Chem. 2003, 7, 275-300.
15. Gribble, G.W. In Name Reactions for Homologations; Li, J.J., Ed., Wiley: Chichester, 2009; Part 2, pp. 749-764.
16. Nájera, C., Sansano, J.M., Yus, M. Tetrahedron 2003, 59, 9255-9303.
17. Chinchilla, R., Nájera, C., Yus, M. Chem. Rev. 2004, 104, 2667-2722.
18. Parham, W.E., Jones, L.D., Sayed, Y.A. J. Org. Chem. 1975, 40, 2394-2399.
19. Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544.
20. Mealy, M.J., Bailey, W.F. J. Organomet. Chem. 2002, 646, 59-67.
21. Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon Press: New York, 2002; pp. 273-335.
22. Normant, J.F. Top. Organomet. Chem. 2003, 287-310.
23. Fañanás, F.J., Sanz, R. In The Chemistry of Organolithium Compounds; Patai Series: The Chemistry of Functional Groups; Rappoport, Z., Marek, I., Eds., Wiley: Chichester, 2006; Vol. 2, Chapter 4, pp. 295-379.
24. Hogan, A.M.L., O'Shea, D.F. Chem. Commun. 2008, 3839-3851.
25. Sanz, R. In Targets in Heterocyclic Systems; Attanasi, O.A., Spinelli, D., Eds., Società Chimica Italiana: Rome, 2008; Vol. 12, pp. 349-389.
26. Gribble, G.W. In Science of Synthesis [Houben-Weyl Methods of Molecular Transformations]; Majewski, M., Snieckus, V., Eds., Georg Thieme Verlag: Sttutgart, 2006; Vol. 8a, pp. 313-327.
27. Rim, C., Son, D.Y. Arkivoc 2006, 265-291.
28. Krief, A., Dumont, W., Gillin, F. Arkivoc 2007, 51-64.
29. Foubelo, F., Yus, M. Chem. Soc. Rev. 2008, 37, 2620-2633.
30. Yus, M. In The Chemistry of Organolithium Compounds; Patai Series: The Chemistry of Functional Groups; Rappoport, Z., Marek, I., Eds., Wiley: Chichester, 2004; Vol. 2, pp. 647-747.
31. Chamberlin, A.R., Bloom, S.H., Cervini, L.A., Fotsch, C.H. J. Am. Chem. Soc. 1988, 110, 4788-4796.
32. Funk, R.L., Bolton, G.L., Brummond, K.M., Ellestad, K.E., Stallman, J.B. J. Am. Chem. Soc. 1993, 115, 7023-7024.
33. Bailey, W.F., Jiang, X.-L., McLeod, C.E. J. Org. Chem. 1995, 60, 7791-7795.
34. Krief, A., Kenda, B., Remacle, B. Tetrahedron 1996, 52, 7435-7463.
35. Coldham, I., Hufton, R., Price, K.N., Rathmell, R.E., Snowden, D.J., Vennall, G.P. Synthesis 2001, 1523-1531.
36. Deng, K., Bensari, A., Cohen, T. J. Am. Chem. Soc. 2002, 124, 12106-12107.
37. Sanz, R., Ignacio, J.M., Rodríguez, M.A., Fañanás, F.J., Barluenga, J. Chem. Eur. J. 2007, 13, 4998-5008.
38. Unkelbach, C., Strohmann, C. J. Am. Chem. Soc. 2009, 17044-17045.
39. Tomida, Y., Nagaki, A., Yoshida, J. Org. Lett. 2009, 11, 3614-3617.
40. Lu, B.-L., Lu, J.-M., Shi, M. Tetrahedron Lett. 2010, 51, 321-324.
41. Bailey, W.F., Ovaska, I.V. Mechanisms of Importance in Synthesis In Advances in Detailed Reaction Mechanism; Coxon, J.M., Ed., JAI Press: Greenwich, CT, 1994; Vol. 3, pp. 251-273.
42. Bailey, W.F., Khanolkar, A.D., Gavaskar, K., Ovaska, T.V., Rossi, K., Thiel, Y., Wiberg, K.B. J. Am. Chem. Soc. 1991, 113, 5720-5727.
43. Rölle, T., Hoffmann, R.W. J. Chem. Soc., Perkin Trans. 2 1995, 1953-1954.
44. Woltering, M.J., Fröhlich, R., Hoppe, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1764-1766.
45. Tomooka, K., Komine, N., Nakai, T. Tetrahedron Lett. 1997, 38, 8939-8942.
46. Zhang, D., Liebeskind, L.S. J. Org. Chem. 1996, 61, 2594-2595.
47. Bailey, W.F., Jiang, X.-L. J. Org. Chem. 1996, 61, 2596-2597.
48. Bailey, W.F., Luderer, M.R., Mealy, M. J. Tetrahedron Lett. 2003, 44, 5303-5305.
49. Bailey, W.F., Salgaonkar, P.D., Brubaker, D., Sharma, V. Org. Lett. 2008, 10, 1071-1074.
50. Commins, D.L., Zhang, Y. J. Am Chem. Soc. 1996, 118, 12248-12249.
51. Barluenga, J., Sanz, R., Granados, A., Fañanás, F.J. J. Am. Chem. Soc. 1998, 120, 4865-4866.
52. Fañanás, F. J; Granados, A., Sanz, R., Ignacio, J.M., Barluenga, J. Chem. Eur. J. 2001, 7, 2896-2907.
53. Bailey, W.F., Punzalan, E.R. Tetrahedron Lett. 1996, 37, 5435-5436.
54. Barluenga, J., Fañanás, F.J., Sanz, R., Marcos, C. Chem. Eur. J. 2005, 11, 5397-5407.
55. Nishiyama, H., Sugimoto, H., Wakita, H., Nagase, H. Synlett 1998, 930-932.
56. Harrowven, D.C. Tetrahedron Lett. 1992, 33, 2879-2882.
57. Bailey, W.F., Mealey, M.J., Wiberg, K.B. Org. Lett. 2002, 4, 791-794.
58. Bailey, W.F., Daskapan, T., Rampalli, S. J. Org. Chem. 2003, 68, 1334-1338.
59. Knochel, P. In Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Semmelhack, M.F., Eds., Pergamon: Oxford, 1991; pp. 865-911.
60. Becker, J.Y. J. Organomet. Chem. 1977, 127, 1-5.
61. Bridson, A.K., Crossley, I.R., Pritchard, R.G., Sadiq, G., Warren, J.E. Organometallics 2003, 22, 5534-5542.
62. Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon: Amsterdam, 2002; Chapter 7, pp. 275-335.
63. Hojo, M., Murakami, Y., Aihara, H., Sakuragi, R., Baba, Y., Hosomi, A. Angew. Chem. Int. Ed. 2001, 40, 621-623.
64. Shirikawa, E., Ikeda, D., Ozawa, T., Watanabe, S., Hayashi, T. Chem. Commun. 2009, 1885-1887.
65. Bailey, W.F., Ovaska, T.V., Leipert, T.K. Tetrahedron Lett. 1989, 30, 3901-3904.
66. Bailey, W.F., Ovaska, T.V. Tetrahedron Lett. 1990, 31, 627-630.
67. Bailey, W.F., Ovaska, T.V. Chem. Lett. 1993, 819.
68. Funk, R.L., Bolton, G.L., Brummond, K.M., Ellestad, K.E., Stallman, J.B. J. Am. Chem. Soc. 1993, 115, 7023-7024.
69. Bailey, W.F., Ovaska, T.V. J. Am. Chem. Soc. 1993, 115, 3080-3090.
70. Ovaska, T.V., Warren, R.R., Lewis, C.E., Wachter-Jurcsak, N.M., Bailey, W.F. J. Org. Chem. 1994, 59, 5868-5870.
71. Bailey, W.F., Wachter-Jurcsak, N.M., Pineau, M.R., Ovaska, T.V., Warren, R.R., Lewis, C.E. J. Org. Chem. 1996, 61, 8216-8228.
72. Kandil; S.A., Dessy, R.E. J. Am. Chem. Soc. 1966, 88, 3027-3034.
73. Johnson, F., Subramanian, R. J. Org. Chem. 1986, 51, 5040-5041.
74. Bailey, W.F., Wachter-Jurcsak, N.M., Pineau, M.R., Ovaska, T.V., Warren, R.R., Lewis, C.E. J. Org. Chem. 1996, 61, 8216-8228.
75. Wu, G., Cederbaum, F.E., Negishi, E. Tetrahedron Lett. 1990, 31, 493-496.
76. Guillam, A., Toupet, L., Maddaluno, J. J. Org. Chem. 1998, 63, 5110-5122.
77. Guillam, A., Toupet, L., Maddaluno, J. J. Org. Chem. 1999, 64, 9348-9357.
78. Le Strat, F., Maddaluno, J. Tetrahedron Lett. 2000, 41, 5367-5371.
79. Le Strat, F., Maddaluno, J. Org. Lett. 2002, 4, 2791-2793.
80. Le Strat, F., Harrowven, D.C., Maddaluno, J. J. Org. Chem. 2005, 70, 489-498.
81. Fressigné, C., Girard, A.-L., Durandetti, M., Maddaluno, J. Chem Eur. J. 2008, 14, 5159-5167.
82. Fressigné, C., Girard, A.-L., Durandetti, M., Maddaluno, J. Angew. Chem. Int. Ed. 2008, 47, 891-893.
83. Fressigné, C., Girard, A.-L., Durandetti, M., Maddaluno, J. Eur. J. Org. Chem. 2009, 721-729.
84. Bailey, W.F., Longstaff, S.C. J. Org. Chem. 1998, 63, 432-433.
85. Bailey, W.F., Longstaff, S.C. Tetrahedron Lett. 1999, 40, 6899-6901.
86. Barluenga, J., Fañanás, F.J., Sanz, R., Fernández, Y. Tetrahedron Lett. 1999, 40, 1049-1052.
87. Barluenga, J., Fañanás, F.J., Sanz, R., Fernández, Y. Chem. Eur. J. 2002, 8, 2034-2046.
88. Sanz, R., Fernández, Y., Castroviejo, M.P., Pérez, A., Fañanás, F.J. J. Org. Chem. 2006, 71, 6291-6294.
89. Bailey, W.F., Patricia, J.J., Del Gobbo, V.C., Jarret, R.M., Okarma, P.J. J. Org. Chem. 1985, 50, 1999-2000.
90. Coldham, I., Vennall, C.P. Chem. Commun. 2000, 1569-1570.
91. Barluenga, J., Sanz, R., Fañanás, F. J. Tetrahedron Lett. 1997, 38, 2763-2766.
92. Sanz, R., Castroviejo, M.P., Miguel, D., Fañanás, F. J. Lett. Org. Chem. 2006, 3, 470-476.
93. Pedrosa, R., Andrés, C., Iglesias, J.M., Pérez-Encabo, A. J. Am. Chem. Soc. 2001, 123, 1817-1821.
94. Collado, M.I., Manteca, I., Sotomayor, N., Villa, M.J., Lete, E. J. Org. Chem. 1997, 62, 2080-2092.
95. González-Temprano, I., Sotomayor, N., Lete, E. Synlett 2002, 593-587.
96. Ruiz, J., Sotomayor, N., Lete, E. Org. Lett. 2003, 5, 1115-1117.
97. Osante, I., Lete, E., Sotomayor, N. Tetrahedron Lett. 2004, 45, 1253-1256.
98. González-Temprano, I., Osante, I., Lete, E., Sotomayor, N. J. Org. Chem. 2004, 69, 3875-3885.
99. Ruiz, J., Ardeo, A., Ignacio, R., Sotomayor, N., Lete, E. Tetrahedron 2005, 61, 3311-3324.
100. Ruiz, J., Sotomayor, N., Lete, E. Tetrahedron 2006, 62, 6182-6189.
101. Abdullah, M.N., Arrasate, S., Lete, E., Sotomayor, N. Tetrahedron 2007, 64, 1329-1332.
102. Lage, S., Villaluenga, I., Sotomayor, N., Lete, E. Synlett 2008, 3188-3192.
103. Mhaske, S.B. Synlett 2005, 184-185.
104. Yamamoto, Y., Maeda, K., Tomimoto, K., Mase, T. Synlett 2002, 561-564.
105. Commins D.L., Huang, S., McArdale, C.L., Ingalls, C.L. Org. Lett. 2001, 3, 469-471.
106. Commins, D.L., Nolan, J.M. Org. Lett. 2001, 3, 4255-4257.
107. Mhaske, S.B., Argade, N.P. J. Org. Chem. 2004, 69, 4563-4566.
108. Naka, H., Akagi, Y., Yamada, K., Imahori, T., Kasahara, T., Kondo, Y. Eur. J. Org. Chem. 2007, 4635-4637.
109. Comins, D.L., Odachi, P.W. Tetrahedron Lett. 2008, 49, 569-572.
110. Kondo, Y., Asai, M., Miura, T., Uchiyama, M., Sakamoto, T. Org. Lett. 2001, 3, 13-15.
111. Martinez-Estibalez, U., Sotomayor, N., Lete, E. Org. Lett. 2009, 11, 1237-1240.
112. Bailey, W.F., Jiang, X. Tetrahedron 2005, 61, 3183-3194.
113. Sanz, R., Fernández, Y., Castroviejo, M.P., Pérez, A., Fañanás, F. J. Eur. J. Org. Chem. 2007, 62-69.
114. Beak, P., Basu, A., Gallagher, D.J., Park, Y.S., Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
115. Hoppe, D., Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282-2316.
116. Beak, P., Anderson, D.R., Curtis, M.D., Lumer, J.M., Pippel, D.J., Weisenburger, G.A. Acc. Chem. Res. 2000, 33, 715-727.
117. Hoppe, D., Christoph, G. In The Chemistry of Organolithiums Compunds; Rappoport, Z., Marek, I. Eds., John Wiley and Sons: New York, 2004; Chapter 17, pp. 1055-1164.
118. Bailey, W.F., Mealy, M.J. J. Am. Chem. Soc. 2000, 122, 6787-6788.
119. Sanz, G., Groth, U.M. J. Am. Chem. Soc. 2000, 122, 6789-6790.
120. Mealy, M.J., Luderer, M.R., Bailey, W.F., Sommer, M.B. J. Org. Chem. 2004, 69, 6042-6049.
121. Groth, U., Koettgen, P., Langenbach, P., Lindenmaier, A., Schuetz, T., Wiegand, M. Synlett 2008, 1301-1304.
122. Barluenga, J., Fañanás, F.J., Sanz, R., Marcos, C. Org. Lett. 2002, 4, 2225-2228.
123. Arrasate, S., Lete, E., Sotomayor, N. Tetrahedron: Asymmetry 2002, 13, 311-316.
124. Liu, H., Deng, K., Cohen, T., Jordan, K.D. Org. Lett. 2007, 9, 1911-1914.