Synthesis and applications of (R)- and (S)-pantolactone as chiral auxiliaries

Current Organic Chemistry

Volumn 8, Issue 14, 2004, Pages 1339-1380

  Camps, Pelayo ^a   Muñoz Torrero, Diego ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCT; PANTOLACTONE;

CHEMICAL PROCEDURES; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOMER; OPTICAL RESOLUTION; ORGANIC CHEMISTRY; RACEMIC MIXTURE; RESEARCH; REVIEW; SYNTHESIS;

EID: 4544328114     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272043369944     Document Type: Review

References (217)

1. Roos, G. Compendium of Chiral Auxiliary Applications, Academic Press: San Diego, 2002.
2. Seyden-Penne, J. Chiral Auxiliaries and Ligandy in Asymmetric Synthesis, John Wiley & Sons: New York, 1995.
3. Stiller, E.T.; Harris, S.A.; Finkelstein, J.; Keresztesy, J.C.; Folkers, K. J. Am. Chem. Soc. 1940, 62, 1785.
4. Beutel, R.; Tishler, M. J. Am. Chem. Soc. 1946, 68, 1463.
5. Ozegowski, W.; Haering, H. Pharmazie 1957, 12, 254.
6. Fizet, C. Helv. Chim. Acta 1986, 69, 404.
7. Toda, F.; Sato, A.; Tanaka, K.; Mak, T.C.W. Chem. Lett. 1989, 873.
8. Vinogradov, M.G.; Kurilov, D.V.; Ferapontov, V.A.; Heise, G.L. Russ. Chem. Bull., Int. Ed. 2000, 49, 1483.
9. Fuji, K.; Node, M.; Murata, M.; Terada, S.; Hashimoto, K. Tetrahedron Lett. 1986, 27, 5381.
10. Achiwa, K.; Kogure, T.; Ojima, I. Tetrahedron Lett. 1977, 4431.
11. Ojima, I.; Kogure, T.; Terasaki, T.; Achiwa, A. J. Org. Chem. 1978, 43, 3444.
12. Takahashi, H.; Hattori, M.; Chiba, M.; Morimoto, T.; Achiwa, K. Tetrahedron Lett. 1986, 27, 4477.
13. Ojima, I.; Kogure, T.; Yoda, Y. Org. Synth. 1985, 63, 18.
14. Morimoto, T.; Takahashi, H.; Fujii, K.; Chiba, M.; Achiwa, K. Chem. Lett. 1986, 2061.
15. Tani, K.; Ise, T.; Tatsuno, Y.; Saito, T. J. Chem. Soc., Chem. Commun. 1984, 1641.
16. Roucoux, A.; Agbossou, F.; Mortreux, A.; Petit, F. Tetrahedron: Asymmetry 1993, 4, 2279.
17. Roucoux, A.; Devocelle, M.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A. Synlett, 1995, 358.
18. Pasquier, C.; Naili, S.; Pelinski, L.; Brocard, J.; Mortreux, A.; Agbossou, F. Tetrahedron: Asymmetry 1998, 9, 193.
19. Pasquier, C.; Pélinski, L.; Brocard, J.; Mortreux, A.; Agbossou-Niedercorn, F. Tetrahedron Lett. 2001, 42, 2809.
20. Roucoux, A.; Suisse, I.; Devocelle, M.; Carpentier, J.-F.; Agbossou, F.; Mortreux, A. Tetrahedron: Asymmetry 1996, 7, 379.
21. Boaz, N.W.; Debenham, S.D.; Mackenzie, E.B.; Large, S.E. Org. Lett. 2002, 4, 2421.
22. Hapiot, F.; Agbossou, F.; Mortreux, A. Tetrahedron: Asymmetry 1994, 5, 515.
23. Genet, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño de Andrade, M.C.; Darses, S.; Galopin, C.; Laffite, J.A. Tetrahedron Asymmetry 1994, 5, 675.
24. Schürch, M.; Schwalm, O.; Mallat, T.; Weber, J.; Baiker, A. J. Catal. 1997, 169, 275.
25. Schürch, M.; Künzle, N.; Mallat, T.; Baiker, A. J. Catal. 1998, 176, 569.
26. Margitfalvi, J.L.; Tfirst, E. J. Mol. Catal. A 1999, 139, 81.
27. Ohno, A.; Ikeguchi, M.; Kimura, T.; Oka, S. J. Am. Chem. Soc. 1979, 101, 7036.
28. Versleijen, J.P.; Sanders-Hovens, M.S.; Vanhommerig, S.A.; Vekemans, J.A.; Meijer, E.M. Tetrahedron 1993, 49, 7793.
29. Heldmann, D.K.; Seebach, D. Helv. Chim. Acta 1999, 82, 1096.
30. Wasmuth, D.; Arigoni, D.; Seebach, D. Helv. Chim. Acta 1982, 65, 344.
31. Paetow, M.; Ahrens H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323.
32. Rama Rao, A.V.; Mahender Rao; S.; Sharma, G.V.M. Tetrahedron Lett. 1994, 35, 5735.
33. Upadhya, T.T.; Gurunath, S.; Sudalai, A. Tetrahedron: Asymmetry 1999, 10, 2899.
34. Pansare, S.V.; Jain, R.P. Org. Lett. 2000, 2, 175.
35. Evans, D.A.; Wu, J.; Masse, C.E.; MacMillan, D.W.C. Org. Lett. 2002, 4, 3379.
36. Martin, S.F.; Dodge, J.A. Tetrahedron Lett. 1991, 32, 3017.
37. Corey, E.J.; Huang, H.-C. Tetrahedron Lett. 1989, 30, 5235.
38. Moriarty, R.M.; Zhuang, H.; Penmasta, R.; Liu, K.; Awasthi, A.K.; Tuladhar, S.M.; Rao, M.S.C.; Singh, V.K. Tetrahedron Lett. 1993, 34, 8029.
39. Calmes, M.; Daunis, J.; Jacquier, R.; Natt, F. Org. Prep. Proced. Int. 1995, 27, 107.
40. Shimizu, T.; Hiranuma, S.; Nakata, T. Tetrahedron Lett. 1996, 37, 6145.
41. Kataoka, M.; Shimizu, K.; Sakamoto, K.; Yamada, H.; Shimizu, S. Appl. Microbiol. Biotechnol. 1995, 43, 974.
42. Shimizu, S.; Kataoka, M. Ann. New York Acad. Sci. 1996, 650.
43. Kesseler, M.; Friedrich, T.; Höffken, H.W.; Hauer, B. Adv. Synth. Catal. 2002, 344, 1103.
44. Shimizu, S.; Hattori, S.; Hata, H.; Yamada, H. Appl. Environ. Microbiol. 1987, 53, 519.
45. Kataoka, M.; Shimizu, S.; Yamada, H. Recl. Trav. Chim. Pays-Bas 1991, 110, 155.
46. Shimizu, S.; Hattori, S.; Hata, H.; Yamada, H. Enzyme Microbiol. Technol. 1987, 9, 411.
47. Eck, R.; Simon, H. Tetrahedron: Asymmetry 1994, 5, 1419.
48. Kataoka, M.; Shimizu, S.; Yamada, H. Agric. Biol. Chem. 1990, 54, 177.
49. Nakamura, K.; Kondo, S.-I. Kawai, Y.; Ohno, A. Tetrahedron: Asymmetry 1993, 4, 1253.
50. Kuhn, R.; Wieland, T. Chem. Ber. 1942, 75, 121.
51. Lanzilotta, R.P.; Bradley, D.G.; McDonald, K.M. Appl. Microbiol. 1974, 27, 130.
52. Shimizu, S.; Yamada, H., Hata, H.; Morishita, T.; Akutsu, S.; Kawamura, M. Agric. Biol. Chem. 1987, 51, 289.
53. Baumann, M.; Hauer, B.H.; Bornscheuer, U.T. Tetrahedron: Asymmetry 2000, 11, 4781.
54. Bevinakatti, H.S.; Banerji, A.A.; Newadkar, R.V. J. Org. Chem. 1989, 54, 2453.
55. Gamalevich, G.D.; Serebryakov, E.P. Russ. Chem. Bull. 1997, 46, 171.
56. Haughton, L.; Williams, J.M.J.; Zimmermann, J.A. Tetrahedron: Asymmetry 2000, 11, 1697.
57. Effenberger, F.; Eichhorn, J.; Roos, J. Tetrahedron: Asymmetry 1995, 6, 271.
58. Krohn, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1582.
59. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I.; Paquette, L.A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp. 315-399.
60. Corey, E.J.; Ensley, H.E. J. Am. Chem. Soc. 1975, 97, 6908.
61. Poll, T.; Hemlchen, G.; Bauer, B. Tetrahedron Lett. 1984, 25, 2191.
62. Poll, T.; Metter, J.O.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 112.
63. Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095.
64. Poll, T.; Abdel Hady, A.F.; Karge, R.; Linz, G.; Weetman, J.; Helmchen, G. Tetrahedron Lett. 1989, 30, 5595.
65. Maruoka, K.; Oishi, M.; Yamamoto, H. Synlett 1993, 683.
66. Maruoka, K.; Oishi, M.; Shiohara, K.; Yamamoto, H. Tetrahedron 1994, 50, 8983.
67. Chang, H.X.; Zhou, L.; McCargar, R.D.; Mahmud, T.; Hirst, I. Org. Proc. Res. Dev. 1999, 3, 289.
68. Cativiela, C.; Figueras, F.; Fraile, J.M.; García, J.I; Mayoral, J.A. Tetrahedron: Asymmetry 1993, 4, 223.
69. Miyaji, K.; Ohara, Y.; Takahashi, Y.; Tsuruda, T.; Arai, K. Tetrahedron Lett. 1991, 32, 4557.
70. Helmchen, G.; Ihrig, K.; Schindler, H. Tetrahedron Lett. 1987, 28, 183.
71. Trost, B.M.; Kondo, Y. Tetrahedron Lett. 1991, 32, 1613.
72. Argenti, L.; Bellina, F.; Carpita, A.; Rossi, R. Synth. Commun. 1995, 25, 2909.
73. Scammells, P.J.; Baker, S.P.; Bellardinelli, L.; Olsson, R.A.; Russell, R.A.; Knevitt, S.A. Bioorg. Med. Chem. Lett. 1996, 6, 811.
74. Toyota, M.; Asoh, T.; Matsuura, M.; Fukumoto, K. J. Org. Chem. 1996, 61, 8687.
75. Hansen, M.M.; Bertsch, C.F.; Harkness, A.R.; Huff, B.E.; Hutchison, D.R.; Khan, V.V.; LeTourneau, M.E.; Martinelli, M.J.; Misner, J.W.; Peterson, B.C.; Rieck, J.A.; Sullivan, K.A.; Wright, I.G. J. Org. Chem. 1998, 63, 775.
76. Mash, E.A.; Gregg, T.M. J. Org. Chem. 1995, 60, 6180.
77. Linz, G.; Weetman, J.; Hady, A.F.A.; Helmchen, G. Tetrahedron Lett. 1989, 30, 5599.
78. Beddoes, R.; Pratt, R.M.; Thomas, E.J. J. Chem. Soc., Perkin Trans. 1 1998, 717.
79. Helmchen, G.; Hady, A.F.A.; Hartmann, H.; Karge, R.; Krotz, A.; Sartor, K.; Urmann, M. Pure Appl. Chem. 1989, 61, 409.
80. Hamley, P.; Helmchen, G.; Holmes, A.B.; Marshall, D.R.; MacKinnon J.W.M.; Smith, D.F.; Ziller, J.W. J. Chem. Soc., Chem. Commun. 1992, 786.
81. Helmchen, G.; Karge, R.; Weetman, J. In Modern Synthetic Methods; Scheffold, R. Ed.; Springer: Heidelberg, 1986; Vol. 4, p. 22.
82. Hanzawa, Y.; Suzuki, M.; Kobayashi, Y.; Taguchi, T.; Iitaka, Y. J. Org. Chem. 1991, 56, 1718.
83. Cativiela, C.; Mayoral, J.A.; Avenoza, A.; Peregrina, J.M.; Lahoz, F.J.; Gimeno, S. J. Org. Chem. 1992, 57, 4664.
84. Cativiela, C.; Avenoza, A.; París, M.; Peregrina, J.M. J. Org. Chem. 1994, 59, 7774.
85. Avenoza, A.; Cativiela, C.; Mayoral, J.A.; Peregrina, J.M. Tetrahedron: Asymmetry 1992, 3, 913.
86. Fraile, J.M.; Garcia, J.I.; Mayoral, J.A.; Pires, E.; Tarnai, T. Catalysis Lett. 1998, 51, 235.
87. Brimble, M.A.; McEwan, J.F.; Turner, P. Tetrahedron: Asymmetry 1998, 9, 1239.
88. Brimble, M.A.; McEwan, J.F. Tetrahedron: Asymmetry 1997, 8, 4069.
89. Brimble, M.A.; Elliot, R.J.; McEwan, J.F. Aust. J. Chem. 2000, 53, 571.
90. Knol, J.; Jansen, J.F.G.A.; van Bolhuis, F.; Feringa, B.L. Tetrahedron Lett. 1991, 32, 7465.
91. Markó, I.E.; Evans, G.R. Tetrahedron Lett. 1994, 35, 2767.
92. Markó, I.E.; Evans, G.R.; Declercq, J.-P. Tetrahedron 1994, 50, 4557.
93. Dujardin, G.; Maudet, M.; Brown, E. Tetrahedron Lett. 1997, 38, 1555.
94. Brown, E.; Dujardin, G.; Maudet, M. Tetrahedron 1997, 53, 9679.
95. Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585.
96. Boccardo, G.; Capozzi, G.; Giuntini, M.; Menichetti, S.; Nativi, C. Tetrahedron 1997, 53, 17383.
97. Rigby, J.H.; Pigge, F.C. J. Org. Chem. 1995, 60, 7392.
98. Fauré, J.-L.; Réau, R.; Wong, M.W.; Koch, R.; Wentrup, C.; Bertrand, G. J. Am. Chem. Soc. 1997, 119, 2819.
99. Savinov, S.N.; Austin, D.J. Org. Lett. 2002, 4, 1415.
100. Cravotto, G.; Giovenzana, G.B.; Pilati, T.; Sisti, M.; Palmisano, G. J. Org. Chem. 2001, 66, 8447.
101. Hanzawa, Y.; Suzuki, M.; Sekine, T.; Murayama, T.; Taguchi, T. J. Chem. Soc., Chem Commun. 1991, 721.
102. Davies, H.M.L.; Cantrell, W.R., Jr. Tetrahedron Lett. 1991, 32, 6509.
103. Davies, H.M.L.; Huby, N.J.S.; Cantrell, W.R., Jr.; Olive, J.L. J. Am. Chem. Soc. 1993, 115, 9468.
104. Davies, H.M.L.; Ahmed, G.; Calvo, R.L.; Churchill, M.R.; Churchill, D.G. J. Org. Chem. 1998, 63, 2641.
105. He, M.; Tanimori, S.; Ohira, S.; Nakayama, M. Tetrahedron 1997, 53, 13307.
106. Moore, J.D.; Sprott, K.T.; Wrobleski, A.D.; Hanson, P.R. Org. Lett. 2002, 4, 2357.
107. Davies, H.M.L. Adv. Cycloadditions 1999, 5, 119.
108. Davies, H.M.L.; Ahmed, G.; Churchill, M.R. J. Am. Chem. Soc. 1996, 118, 10774.
109. Davies, H.M.L.; Huby, N.J.S. Tetrahedron Lett. 1992, 33, 6935.
110. Davies, H.M.L.; Matasi, J.J.; Hodges, L.M.; Huby, N.J.S.; Thornley, C.; Kong, N.; Houser, J.H. J. Org. Chem. 1997, 62, 1095.
111. Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett. 1994, 35, 9549.
112. Bulugahapitiya, P.; Landais, Y.; Parra-Rapado, L.; Planchenault, D.; Weber, V. J. Org. Chem. 1997, 62, 1630.
113. Doyle, M.P.; Yan, M. Tetrahedron Lett. 2002, 43, 5929.
114. Landais, Y.; Planchenault, D. Tetrahedron 1997, 53, 2855.
115. Ye, T.; McKervey, A.; Brandes, B.D.; Doyle, M.P. Tetrahedron Lett. 1994, 35, 7269.
116. Lee, S.; Lim, H.-J.; Cha, K.L.; Sulikowski, G.A. Tetrahedron 1997, 53, 16521.
117. Hervouet, K.; Guingant, A. Tetrahedron: Asymmetry 1996, 7, 425.
118. Brimble, M.A.; McEwan, J.F.; Turner, P. Tetrahedron: Asymmetry 1998, 9, 1257.
119. Nimkar, K.S.; Mash, E.A. Tetrahedron 2000, 56, 5793.
120. Yim, A.-M.; Vidal, Y.; Viallefont, P.; Martinez, J. Tetrahedron: Asymmetry 2002, 13, 503.
121. Khan, A.A.; Emslie, N.D.; Drewes, S.E.; Field, J.S.; Ramesar, N. Chem. Ber. 1993, 126, 1477.
122. Greaney, M.F.; Motherwell, W.B. Tetrahedron Lett. 2000, 41, 4463.
123. Koh, K.; Ben, R.N.; Durst, T. Tetrahedron Lett. 1993, 34, 4473.
124. O'Meara, J.A.; Gardee, N.; Jung, M.; Ben, R.N.; Durst, T. J. Org. Chem. 1998, 63, 3117.
125. Ben, R.N.; Durst, T. J. Org. Chem. 1999, 64, 7700.
126. Koh, K.; Ben, R.N.; Durst, T. Tetrahedron Lett. 1994, 35, 375.
127. Ammazzalorso, A.; Amoroso, R.; Bettoni, G.; de Filipis, B. Chirality 2001, 13, 102.
128. Koh, K.; Durst, T. J. Org. Chem. 1994, 59, 4683.
129. Amoroso, R.; Bettoni, G.; Tricca, M.L. Synlett 1998, 363.
130. Besson, M.; Gallezot, P.; Neto, S.; Pinel, C. Tetrahedron: Asymmetry 2000, 11, 1809.
131. Douja, N.; Besson, M.; Gallezot, P.; Pinel, C. J. Mol. Catal. A: Chemical 2002, 186, 145.
132. Hassine, B.B.; Gorsane, M.; Pecher, J.; Martin, R.H. Bull. Soc. Chim. Belg. 1985, 94, 759.
133. Larsen, R.D.; Corley, E.G.; Davis, P.; Reider, P.J.; Grabowski, E.J.J. J. Am. Chem. Soc. 1989, 111, 7650.
134. Senanayake, C.H.; Larsen, R.D.; Bill, T.J.; Liu, J.; Corley, E.G.; Reider, P.J. Synlett 1994, 199.
135. Calmes, M.; Daunis, J.; Jacquier, R.; Natt, F. Tetrahedron 1994, 50, 6875.
136. Meyer, M.D.; Hancock, A.A.; Tietje, K.; Sippy, K.B.; Prasad, R.; Stout, D.M.; Arendsen, D.L.; Donner, B.G.; Carroll, W.A. J. Med. Chem. 1997, 40, 1049.
137. Durst, T.; Koh, K. Tetrahedron Lett. 1992, 33, 6799.
138. Calmes, M.; Daunis, J.; Mai, N.; Natt, F. Tetrahedron Lett. 1996, 37, 379.
139. Calmes, M.; Daunis, J.; Mai, N. Tetrahedron: Asymmetry 1997, 8, 1641.
140. Calmes, M.; Daunis, J.; Mai, N. Tetrahedron 1997, 53, 13719.
141. Calmes, M.; Escale, F. Tetrahedron: Asymmetry 1998, 9, 2845.
142. Calmes, M.; Escale, F.; Glot, C.; Rolland, M.; Martinez, J. Eur. J. Org. Chem. 2000, 2459.
143. Calmes, M.; Escale, F.; Martinez, J. Tetrahedron: Asymmetry 2002, 13, 293.
144. Calmes, M.; Escale, F.; Juan, E.; Rolland, M.; Martinez, J. Tetrahedron: Asymmetry 2000, 11, 1263.
145. Cannizzaro, C.E.; Strassner, T.; Houk, K.N. J. Am. Chem. Soc. 2001, 123, 2668.
146. Gerlach, U.; Hünig, S. Angew. Chem., Int. Ed. Engl. 1987, 26, 1283.
147. Gerlach, U.; Haubenreich T.; Hünig, S. Chem. Ber. 1994, 127, 1969.
148. Gerlach, U.; Haubenreich T.; Hünig, S. Chem. Ber. 1994, 127, 1981.
149. Gerlach, U.; Haubenreich T.; Hünig, S.; Klaunzer, N. Chem. Ber. 1994, 127, 1989.
150. Cavelier, F.; Gomez, S.; Jacquier, R.; Verducci, J. Tetrahedron: Asymmetry 1993, 4, 2501.
151. Duhamel, L.; Duhamel, P.; Launay, J.C.; Plaquevent, J.C. Bull. Soc. Chim. Fr. II 1984, 421.
152. Calmès, M.; Glot, C.; Martinez, J. Tetrahedron: Asymmetry 2001, 12, 49.
153. Matsumoto, K.; Ohta, H. Tetrahedron Lett. 1991, 32, 4729.
154. Mikami, K.; Yoshida, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 858.
155. Mikami, K.; Yoshida, A. Tetrahedron 2001, 57, 889.
156. Bargiggia, F.; Piva, O. Tetrahedron: Asymmetry 2001, 12, 1389.
157. Bargiggia, F.; Dos Santos, S.; Piva, O. Synthesis 2002, 427.
158. Allan, R.D.; Fong, J. Aust. J. Chem. 1986, 39, 855.
159. Allan, R.D.; Bates, M.C.; Drew, C.A.; Duke, R.K.; Hambley, T.W.; Johnston, G.A.R.; Mewett, K.N.; Spence, I. Tetrahedron 1990, 46, 2511.
160. Duke, R.K.; Allan, R.D.; Chebib, M.; Greenwood, J.R.; Johnston, G.A.R. Tetrahedron: Asymmetry 1998, 9, 2533.
161. Khouili, M.; Gillaumet, G.; Coudert, G.; Pujol, M.D. Farmaco 1996, 51, 185.
162. Vázquez, M.T.; Rosell, G.; Pujol, M.D. Eur. J. Med. Chem. 1997, 32, 529.
163. Bolognesi, M.L.; Budriesi, R.; Cavalli, A.; Chiarini, A.; Gotti, R.; Leonardi, A.; Minarini, A.; Poggesi, E.; Recanatini, M.; Rosini, M.; Tumiatti, V.; Melchiorre, C. J. Med. Chem. 1999, 42, 4214.
164. Duke, C.C.; Wells, R.J. Aust. J. Chem. 1987, 40, 1641.
165. Altenbach, H.-J.; Merhof, G.F.; Brauer, D.J. Tetrahedron: Asymmetry 1996, 7, 2493.
166. Amoroso, R.; Bettoni, G.; Tricca, M.L.; Loiodice, F.; Ferorelli, S. Farmaco 1998, 53, 73.
167. Jiang, X.; Covey, D.F. J. Org. Chem. 2002, 67, 4893.
168. Reddy, R.; Jaquith, J.B.; Neelagiri, V.R.; Saleh-Hanna, S.; Durst, T. Org. Lett. 2002, 4, 695.
169. Kitagawa, O.; Momose, S.-I.; Fushimi, Y.; Taguchi, T. Tetrahedron Lett. 1999, 40, 8827.
170. Yin, J.; Liebeskind, L.S. J. Am. Chem. Soc. 1999, 121, 5811.
171. Malinakova, H.C.; Liebeskind, L.S. Org. Lett. 2000, 2, 3909.
172. Gómez Arrayás, R.; Liebeskind, L.S. J. Am. Chem. Soc. 2001, 123, 6185.
173. Miranda, M.A.; Martínez, L.A.; Samadi, A.; Boscá, F.; Morera, I.M. Chem. Commun. 2002, 280.
174. Gourdel-Martin, M.-E.; Comoy, C.; Huet. F. Tetrahedron: Asymmetry 1999, 10, 403.
175. Vedejs, F.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
176. Peng, Z.-H.; Woerpel, K.A. Org. Lett. 2002, 4, 2945.
177. Lavallée, P.; Ruel, R.; Grenier, L.; Bissonnette, M. Tetrahedron Lett. 1986, 27, 679.
178. Roy, R.; Rey, A.W.; Charron, M.; Molino, R. J. Chem. Soc., Chem. Commun. 1989, 1308.
179. De Brabander, J.; Vanhessche, K.; Vanderwalle, M. Tetrahedron Lett. 1991, 32, 2821.
180. O'Brien, M.; Taylor, N.H.; Thomas, E.J. Tetrahedron Lett. 2002, 43, 5491.
181. Martin, N.; Thomas, E.J. Tetrahedron Lett. 2001, 42, 8373.
182. Trost, B.M.; Flygare, J.A. Tetrahedron Lett. 1994, 35, 4059.
183. Nakata, T.; Fukui, H.; Nakagawa, T.; Matsukura, H. Heterocycles 1996, 42, 159.
184. Sone, H.; Suenaga, K.; Bessho, Y.; Kondo, T.; Kigoshi, H.; Yamada, K. Chem. Lett. 1998, 85.
185. Shiina, I.; Shibata, J.; Ibuka, R.; Imai, Y.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2001, 74, 113.
186. Tokuzaki, K.; Kanemitu, Y.; Yoshimitsu, T.; Nagaoka, H. Tetrahedron Lett. 2000, 41, 5923.
187. Organ, M.G.; Wang, J. J. Org. Chem. 2002, 67, 7847.
188. Freskos, J.N. Synth. Commun. 1994, 557.
189. Dioubankova, N.N.; Malakhov, A.D.; Stetsenko, D.A.; Korshun, V.A.; Gait, M.J. Org. Lett. 2002, 4, 4607.
190. Hoeper, F.; Montforts, F.-P. Tetrahedron: Asymmetry 1993, 4, 1439.
191. Pansare, S.V.; Bhattacharyya, A. Tetrahedron Lett. 2001, 42, 9265.
192. Tadano, K.-I.; Kanazawa, S.; Ogawa, S. J. Org. Chem. 1988, 53, 3868.
193. Kopelevich, V.M.; Bulanova, L.N.; Gunar, V.I. Chem. Nat. Compd. 1982, 18, 215.
194. Kopelevich, V.M.; Bulanova, L.N.; Gunar, V.I. Tetrahedron Lett. 1979, 3893.
195. Ryan, C.W.; Ainsworth, C. J. Org. Chem. 1962, 27, 2901.
196. Marieva, T.D.; Kopelevich, V.M.; Torosyan, Zh.K.; Gunar, V.I.; J. Gen. Chem. USSR 1979, 49, 191.
197. Hollenberg, N.; Grahn, W.; Jones, P.G. Acta Cryst. 1997, C53, 1851.
198. Camps, P.; Giménez, S.; Font-Bardia, M., Solans, X. Tetrahedron: Asymmetry 1995, 6, 985.
199. Camps, P.; Pérez, F.; Soldevilla, N. Tetrahedron Lett. 1999, 40, 6853.
200. Camps, P.; Font-Bardia, M.; Giménez, S.; Pérez, F.; Solans, X.; Soldevilla, N. Tetrahedron: Asymmetry 1999, 10, 3123.
201. Camps, P.; Pérez, F.; Soldevilla, N. Tetrahedron: Asymmetry 1997, 8, 1877.
202. Camps, P.; Pérez, F.; Soldevilla, N. Tetrahedron: Asymmetry 1998, 9, 2065.
203. Camps, P.; Pérez, F.; Soldevilla, N.; Borrego, M.A. Tetrahedron: Asymmetry 1999, 10, 493.
204. Camps, P.; Giménez, S. Tetrahedron: Asymmetry 1995, 6, 991.
205. Camps, P.; Giménez, S. Tetrahedron: Asymmetry 1996, 7, 1227.
206. Calmes, M.; Glot, C.; Michel, T.; Rolland, M.; Martinez, J. Tetrahedron: Asymmetry 2000, 11, 737.
207. Akkari, R.; Calmes, M.; Mai, N.; Rolland, M.; Martinez, J. J. Org. Chem. 2001, 66, 5859.
208. Barrios, I.; Camps, P.; Comes-Franchini, M.; Muñoz-Torrero, D.; Ricci, A.; Sanchez, L. Tetrahedron 2003, 59, 1971.
209. Brunner, H.; Zettler, C.; Zabel, M. Z. Anorg. Allg. Chem. 2003, 629, 1131.
210. Gizecki, P.; Dhal, R.; Poulard, C.; Gosselin, P.; Dujardin, G. J. Org. Chem. 2003, 68, 4338.
211. Moore, J.D.; Hanson, P.R. Tetrahedron: Asymmetry 2003, 14, 873.
212. Akiyama, T.; Ogi, S.; Fuchibe, K. Tetrahedron Lett. 2003, 44, 4011.
213. Kanoh, N.; Tomatsu, A.; Nishikawa, T.; Ide, M.; Tsuchida, T.; Isshiki, K.; Nakata, M. Tetrahedron: Asymmetry 2003, 14, 1251.
214. Chen, C.-Y.; Dagneau, P.; Grabowski, E.J.J.; Oballa, R.; O'Shea, P.; Prasit, P.; Robichaud, J.; Tillyer, R.; Wang, X. J. Org. Chem. 2003, 68, 2633.
215. Camps, P.; Muñoz-Torrero, D.; Sánchez, L. Tetrahedron: Asymmetry 2004, 15, 311.
216. Calmès, M.; Escale, F.; Rolland, M.; Martinez, J. Tetrahedron: Asymmetry 2003, 14, 1685.
217. Akbutina, F.A.; Sadretdinov, I.F.; Selezneva, N.K.; Miftakhov, M.S. Mendeleev Commun. 2003, 151.