Selectivity controls in the [4+2] cycloadditions of 1-oxygenated dienes

Synlett

Volumn , Issue 16, 2006, Pages 2534-2547

  Maddaluno, Jacques ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

Author keywords

Cycloaddition; Diastereoselectivity; Diels Alder reactions; Dienes; Regioselectivity

Indexed keywords

ALKADIENE;

ARTICLE; CATALYSIS; CYCLOADDITION; DIELS ALDER REACTION;

EID: 33750044890     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950445     Document Type: Article

References (176)

1. General reviews on the Diels-Alder reaction: (a) Sauer, J. Angew. Chem., Int. Ed. Engl. 1967, 6, 16.
2. (b) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990.
3. Trost, B. M.; Fleming, I. Comprehensive Organic Synthesis; Oppolzer, W., Ed.; Pergamon Press: Oxford, 1991.
4. (d) Fringuelli, F.; Taticchi, A. The Diels-Alder Reaction; Wiley and Sons: Chichester, 2002.
5. (e) Applications of the Diels-Alder reaction to total synthesis: Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem. Int. Ed. 2002, 41, 1668.
6. (f) Biosynthetic Diels-Alder reactions: Stocking, E. M.; Williams, R. M. Angew. Chem. Int. Ed 2003, 42, 3078.
7. Recent reviews on the asymmetric Diels-Alder reaction: (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
8. (b) Jurczak, J.; Bauer, T.; Chapuis, C. Stereoselective Synthesis, In Houben-Weyl, Vol. E 21; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1998.
9. (c) Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Spinger: Berlin, 1999, Chap. 33.1.
10. Willis, M. C. In Asymmetric Catalysis; Sainsbury, M., Ed.; Elsevier: Amsterdam, 2001, Chap. 8.
11. (e) Hayashi, Y. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002, Chap. 1.
12. (f) Corey, E. J. Angew. Chem. Int. Ed. 2002, 41, 1650.
13. Petrzilka, M.; Grayson, J. I. Synthesis 1981, 753.
14. Deagostino, A.; Prandi, C.; Zavattaro, C.; Venturello, P. Eur. J. Org. Chem. 2006, 2463.
15. For very recent developments involving this diene, see: Lin, L.; Fan, Q.; Qin, B.; Feng, X. J. Org. Chem. 2006, 71, 4141.
16. Recent reviews on the cycloaddition of furans: (a) Keay, B. A.; Hunt, I. R. Adv. Cycloadd. 1999, 6, 173.
17. (b) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179.
18. Review on cycloaddition of 2-pyrones: Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111.
19. Reviews on photoeneols: (a) Sammes, P. G. Tetrahedron 1976, 32, 405.
20. (b) Funk, R. L.; Volhardt, K. P. C. Chem. Soc. Rev. 1980, 41.
21. For the asymmetric cycloaddition of an oxygenated o-quinodimethane, see: (a) Ito, Y.; Amino, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1983, 105, 1586.
22. (b) Charlton, J. L. Tetrahedron Lett. 1985, 26, 3413.
23. Recent reviews on the hetero-Diels-Alder reaction: (a) Ooi, T.; Maruoka, K. In Comprehensive Asymmetric Catalysis, Vol. 3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Spinger: Berlin, 1999, Chap. 33.2.
24. (b) Jørgensen, K. A. Angew. Chem. Int. Ed. 2000, 39, 3558.
25. (c) Jørgensen, K. A. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002, Chap. 4.
26. (d) Kobayashi, S. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002, Chap. 5.
27. (e) Jørgensen, K. A. Eur. J. Org. Chem. 2004, 2093.
28. (f) About the HDA of 1-oxa-1,3-butadienes, see: Tietze, L. F.; Kettschau, G.; Gewert, J. A.; Schuffenhauer, A. Curr. Org. Chem. 1998, 2, 19.
29. (a) Wichterle, O. Coll. Czech. Chem. Commun. 1938, 10, 497.
30. (b) Flaig, W. Justus Liebigs Ann. Chem. 1950, 568, 1.
31. Dockendorff, C.; Sahli, S.; Olsen, M.; Milhau, L.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 15028.
32. Blain, M.; Odiot, S.; Martin, G. J.; Gouesnard, J. P. Tetrahedron 1980, 36, 2663.
33. Sustmann, R.; Tappanchai, S.; Bandmann, H. J. Am. Chem. Soc. 1996, 118, 12555.
34. Danishefsky, S.; Schuda, P.; Kato, K. J. Org. Chem. 1976, 41, 1081.
35. Fujita, R.; Oikawa, K.; Yoshisuji, T.; Okuyama, Y.; Nakano, H.; Matsuzaki, H. Chem. Pharm. Bull. 2003, 51, 295.
36. Branchadell, V.; Sodupe, M.; Ortuño, R. M.; Oliva, A.; Gomez-Pardo, D.; Guingant, A.; d'Angelo, J. J. Org. Chem. 1991, 56, 4135.
37. Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219.
38. Recent compilation on cycloadditions under high pressure: Matsumoto, K.; Hamana, H.; Iida, H. Helv. Chim. Acta 2005, 88, 2033.
39. Dauben, W. G.; Krabbenhoft, H. O. J. Org. Chem. 1977, 42, 282.
40. (a) Rigby, J. H.; Kierkus, P. C. J. Am. Chem. Soc. 1989, 111, 4125.
41. (b) Rigby, J. H.; Kierkus, P. C.; Head, D. Tetrahedron Lett. 1989, 30, 5073.
42. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; J. Wiley and Sons: Chichester, 1976.
43. (a) Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779.
44. (b) Damoun, S.; Van de Woude, G.; Méndez, F.; Geerlings, P. J. Phys. Chem. A 1997, 101, 886.
45. (c) Dumont, E.; Chaquin, P. J. Mol. Struct. (Theochem) 2006, in press.
46. See for instance: Steiner, G.; Huisgen, R. J. Am. Chem. Soc. 1973, 95, 5056.
47. See for instance: (a) Kahn, S. D.; Pau, C. F.; Overman, L. E.; Hehre, W. J. J. Am. Chem. Soc. 1986, 108, 7381.
48. (b) Tolstikov, G. A.; Shults, E. E.; Malikova, T. S.; Spirikhin, L. V. Mendeleev Commun. 1994, 60.
49. (a) Schmidt, C.; Sabnis, S. D.; Schmidt, E.; Taylor, D. K. Can. J. Chem. 1971, 49, 371.
50. (b) Broekhuis, A. A.; Scheeren, J. W.; Nivard, R. J. F. Rec. Trav. Chim. Pays-Bas 1980, 99, 6.
51. See for instance: (a) Suárez, D.; Sordo, J. A. Chem. Commun. 1998, 385.
52. (b) Imade, M.; Hirao, H.; Omoto, K.; Fujimoto, H. J. Org. Chem. 1999, 64, 6697.
53. Garcia, J. I.; Mayoral, J. A.; Salvatella, L. Acc. Chem. Res. 2000, 33, 658.
54. (d) Arrieta, A.; Cossío, F. P.; Lecea, B. J. Org. Chem. 2001, 66, 6178.
55. (e) Ogawa, A.; Fujimoto, H. Tetrahedron Lett. 2002, 43, 2055.
56. (f) Garcia, J. I.; José Antonio Mayoral, J. A.; Salvatella, L. Eur. J. Org. Chem. 2005, 85.
57. Iwaoka, T.; Katagiri, N.; Sato, M.; Kaneko, C. Chem. Pharm. Bull. 1992, 40, 2319.
58. Hirsenkorn, R.; Haag-Zeino, B.; Schmidt, R. R. Tetrahedron Lett. 1990, 31, 4433.
59. (a) Stork, G.; Hudrlik, P. F. J. Am. Chem. Soc. 1968, 90, 4462.
60. (b) House, H. O.; Czuba, L. J.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1969, 34, 2324.
61. Sodeoka, M.; Yamada, H.; Shibasaki, M. J. Am. Chem. Soc. 1990, 112, 4906.
62. Alder, K.; Stein, G. Angew. Chem. 1937, 50, 510.
63. Rücker, C.; Lang, D.; Sauer, J.; Friege, H.; Sustmann, R. Chem. Ber. 1980, 113, 1663.
64. Mandai, T.; Osaka, K.; Kawagishi, M.; Kawada, M.; Otera, J. J. Org. Chem. 1984, 49, 3595.
65. Balma Tivola, P.; Deagostino, A.; Fenoglio, C.; Mella, M.; Prandi, C.; Venturello, P. Eur. J. Org. Chem. 1999, 2143.
66. Inagaki, S.; Ikeda, H. J. Org. Chem. 1998, 63, 7820.
67. Volle, J.-N.; Schlosser, M. Eur. J. Org. Chem. 2002, 1490.
68. Trost, B. M.; Ippen, J.; Vladuchick, W. C. J. Am. Chem. Soc. 1977, 99, 8116.
69. Maddaluno, J.; Gaonac'h, O.; Marcual, A.; Toupet, L.; Giessner-Prettre, C. J. Org. Chem. 1996, 61, 5290.
70. Revial, G.; Blanchard, M.; d'Angelo, J. Tetrahedron Lett. 1983, 24, 899.
71. Maddaluno, J.; d'Angelo, J. Tetrahedron Lett. 1983, 24, 895.
72. Ferroud, C.; Revial, G.; d'Angelo, J. Tetrahedron Lett. 1985, 26, 3981.
73. Guingant, A.; d'Angelo, J. Tetrahedron Lett. 1986, 27, 3729.
74. Grieco, P. A.; Yoshida, K.; He, Z.-m. Tetrahedron Lett. 1984, 25, 5715.
75. Devine, P. N.; Oh, T. J. Org. Chem. 1991, 56, 1955.
76. Birney, D.; Lim, T. K.; Koh, J. H. P.; Pool, B. R.; White, J. M. J. Am. Chem. Soc. 2002, 124, 5091.
77. Tian, G. R.; Sugiyama, S.; Mori, A.; Takeshita, H. Chem. Lett. 1987, 1557.
78. Rigby, J. H.; Ogbu, C. O. Tetrahedron Lett. 1990, 31, 3385.
79. Koerner, M.; Rickborn, B. J. Org. Chem. 1990, 55, 2662.
80. Rigaudy, J.; Cuong, N. K.; Albouy, J.-P.; Chétrit, A. Tetrahedron Lett. 1976, 1089.
81. Meek, J. S.; Monroe, P. A.; Bouboulis, C. J. J. Org. Chem. 1963, 28, 2572.
82. Knapp, S.; Ornaf, R. M.; Rodriques, K. E. J. Am. Chem. Soc. 1983, 105, 5494.
83. Imashiro, F.; Hirayama, K.; Saika, A. J. Am. Chem. Soc. 1987, 109, 729.
84. Narasaka, K.; Shimada, S.; Osoda, K.; Iwasawa, N. Synthesis 1981, 1171.
85. See for instance: (a) Pollart, D. J.; Moore, H. W. J. Org. Chem. 1989, 54, 5444.
86. (b) McKelvey, T. A.; Czamik, A. W.; Chung, Y. Bull. Korean Chem. Soc. 1997, 18, 457.
87. See inter alia: (a) Kelly, T. R. Tetrahedron Lett. 1978, 1387.
88. (b) Farina, F.; Prados, P. Tetrahedron Lett. 1979, 477.
89. Trost, B. M.; Caldwell, C. G.; Murayama, E.; Heissler, D. J. Org. Chem. 1983, 48, 3252.
90. Kelly, T. R.; Saha, J. K.; Whittle, R. R. J. Org. Chem. 1985, 50, 3679.
91. (e) Kraus, G. A.; Walling, J. A. Tetrahedron Lett. 1986, 27, 1873.
92. (f) Larsen, D. S.; Stoodley, R. J. Tetrahedron 1990, 46, 4711.
93. Laugraud, S.; Guingant, A.; d'Angelo, J. Tetrahedron Lett. 1989, 30, 83.
94. Mulzer, J.; Altenbach, H.-J.; Braum, M.; Krohn, K.; Reissig, H.-U. Organic Synthesis Highlights; VCH: Weinheim, 1991.
95. Gawley, R. E.; Aube, J. Principles of Asymmetric Synthesis; Pergamon: Oxford, 1996.
96. Kahn, S. D.; Herhe, W. J. J. Am. Chem. Soc. 1987, 109, 663.
97. Rück-Braun, K.; Kunz, H. Chiral Auxiliaries in Cycloadditions; Wiley-VCH: Weinheim, 1998.
98. Rieger, R.; Breitmaier, E. Synthesis 1990, 697.
99. Zadel, G.; Rieger, R.; Breitmaier, E. Liebigs Ann. Chem. 1991, 1343.
100. Rotscheid, K.; Breitmaier, E. Synthesis 1989, 836.
101. Virgili, P.; Pericàs, M. A.; Moyano, A.; Riera, A. Tetrahedron 1997, 53, 13427.
102. Trost, B. M.; Godleski, S. A.; Genêt, J.-P. J. Am. Chem. Soc. 1978, 100, 3930.
103. Trost, B. M.; O'Krongly, D.; Belletire, J. L. J. Am. Chem. Soc. 1980, 102, 7595.
104. Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257.
105. Siegel, C.; Thornton, E. R. Tetrahedron Lett. 1988, 29, 5225.
106. Maddaluno, J.; Gresh, N.; Giessner-Prettre, C. J. Org. Chem. 1994, 59, 793.
107. See for instance: (a) Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature (London) 2003, 424, 146.
108. (b) Thadani, A. N.; Stankovic, A. R.; Rawal, V. H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5846.
109. (c) Unni, A. K.; Takenaka, N.; Yamamoto, H.; Rawal, V. H. J. Am. Chem. Soc. 2005, 127, 1336.
110. (a) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1990, 112, 6743.
111. (b) Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 7630.
112. Aspinall, I. H.; Cowley, P. M.; Stoodley, R. J. Tetrahedron Lett. 1994, 35, 3397.
113. (a) Burnouf, C.; Lopez, J. C.; Calvo-Flores, F. G.; de Los Angeles Laborde, M.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1990, 823.
114. (b) Lopez, J. C.; Lukacs, G. In Cycloaddition Reactions in Carbohydrate Chemistry; Giuliano, R. M., Ed.; ACS Symposium Series 494, American Chemical Society: Washington DC, 1992, 33.
115. Arce, E.; Carreño, M. C.; Cid, M. B.; Garcia Ruano, J. L. J. Org. Chem. 1994, 59, 3421.
116. (a) Adams, H.; Jones, D. N.; Aversa, M. C.; Bonaccorsi, P.; Giannetto, P. Tetrahedron Lett. 1993, 34, 6481.
117. (b) Aversa, M. C.; Bonaccorsi, P.; Giannetto, P.; Jones, D. N. Tetrahedron: Asymmetry 1994, 5, 805.
118. (c) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Jones, D. N. J. Org. Chem. 1997, 62, 4376.
119. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Panzalorto, M.; Rizzo, S. Tetrahedron: Asymmetry 1998, 9, 1577.
120. (a) Martin, C.; Maddaluno, J.; Duhamel, L. Tetrahedron Lett. 1996, 37, 8169.
121. (b) Guillam, A.; Toupet, L.; Maddaluno, J. J. Org. Chem. 1998, 63, 5110.
122. See for instance: (a) Tolstikov, G. A.; Shultz, E. E.; Spirikhin, L. V. Tetrahedron 1986, 42, 591.
123. (b) Kim, K. J.; Hahn, S. J.; Lyu, H. S. Bull. Korean Chem. Soc. 1986, 7, 166.
124. (c) Jeong, I. H.; Kim, Y. S.; Cho, K. Y.; Kim, K. J. Bull. Korean Chem. Soc. 1990, 11, 258.
125. (d) Pindur, U.; Keilhofer, D. Liebigs Ann. Chem. 1993, 947.
126. Chen, W.; Strahan, G. D.; Parrish, D. A.; Deschamps, J. R.; Coop, A. Tetrahedron Lett. 2005, 46, 131.
127. Baldwin, S. W.; Greenspan, P.; Alaimo, C.; McPhail, A. T. Tetrahedron Lett. 1991, 32, 5877.
128. Alonso, I.; Carretero, J. C.; Ruano, J. L. G. J. Org. Chem. 1994, 59, 1499.
129. Wolter, M.; Borm, C.; Merten, E.; Wartchow, R.; Winterfeldt, E. Eur. J. Org. Chem. 2001, 4051.
130. Card, P. J. J. Org. Chem. 1982, 47, 2169.
131. Masamune, S.; Reed, L. A. III; Davis, J. T.; Choy, W. J. Org. Chem. 1983, 48, 4441.
132. Franck, R. W.; Subramaniam, C. S.; John, T. V.; Blount, J. F. Tetrahedron Lett. 1984, 23, 2439.
133. Ortuño, R. M.; Guingant, A.; d'Angelo, J. Tetrahedron Lett. 1988, 29, 6989.
134. Ortuño, R. M.; Ibarzo, J.; d'Angelo, J.; Dumas, F.; Alvarez-Larena, A.; Piniella, J. F. Tetrahedron: Asymmetry 1996, 7, 127.
135. Shibata, J.; Shiina, I.; Mukaiyama, T. Chem. Lett. 1999, 313.
136. (a) Qian, W.; Rubin, Y. Angew. Chem. Int. Ed. 1999, 38, 2356.
137. (b) Qian, W.; Rubin, Y. J. Org. Chem. 2002, 67, 7683.
138. Guillam, A.; Toupet, L.; Maddaluno, J. J. Org. Chem. 1999, 64, 9348.
139. (a) Kelly, T. R.; Montury, M. Tetrahedron Lett. 1978, 4309.
140. (b) Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825.
141. Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510.
142. Takasu, M.; Yamamoto, H. Synlett 1990, 194.
143. Bienaymé, H.; Longeau, A. Tetrahedron 1997, 53, 9637.
144. Bienaymé, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2670.
145. Kraus, G. A.; Sugimoto, H. Tetrahedron Lett. 1977, 3929.
146. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812.
147. Giessert, A. J.; Snyder, L.; Markham, J.; Diver, S. T. Org. Lett. 2003, 5, 1793.
148. Breuning, M.; Corey, E. J. Org. Lett. 2001, 3, 1559.
149. Evans, D. A.; Names, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S. J.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582.
150. Kanemasa, S.; Oderaotoshi, Y.; Sakaguchi, S.-i.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074.
151. See for instance: Houk, K. N.; List, B. Acc. Chem. Res. 2004, 37, 487; and papers in this special issue dedicated to organocatalysis.
152. (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
153. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458.
154. Colonna, S.; Manfredi, A.; Annunziata, R. Tetrahedron Lett. 1988, 29, 3347.
155. For reviews on intramolecular Diels-Alder reactions, see: (a) Bear, B. R.; Sparks, S. M.; Shea, K. J. Angew. Chem. Int. Ed. 2001, 40, 821.
156. (b) Craig, D. Chem. Soc. Rev. 1987, 16, 187.
157. (c) Ciganek, E. Org. React. 1984, 32, 1.
158. See for instance: (a) Craig, D.; Reader, J. C. Tetrahedron Lett. 1992, 33, 4073.
159. (b) Stork, G.; Chan, T. Y. J. Am. Chem. Soc. 1995, 117, 6595.
160. (c) Bertozzi, F.; Olsson, R.; Frejd, T. Org. Lett. 2000, 2, 1283.
161. (d) For a review: Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253.
162. Gillard, J. W.; Fortin, R.; Grimm, E. L.; Maillard, M.; Tjepkema, M.; Bernstein, M. A.; Glaser, R. Tetrahedron Lett. 1991, 32, 1145.
163. Deagostino, A.; Maddaluno, J.; Prandi, C.; Venturello, P. J. Org. Chem. 1996, 21, 7597.
164. Aime, S.; Oulyadi, H.; Maddaluno, J.; Venturello, P. Org. Lett. 1999, 1, 1631.
165. Deagostino, A.; Prandi, C.; Venturello, P. Synthesis 1998, 1149.
166. Sparks, S. M.; Shea, K. J. Org. Lett. 2001, 3, 2265.
167. Schoenen, F. J.; Porco, J. A.; Schreiber, S. L. Tetrahedron Lett. 1989, 30, 3765.
168. (a) Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631.
169. (b) Schreiber, S. L.; Kiessling, L. L. Tetrahedron Lett. 1989, 30, 433.
170. (a) Nicolaou, K. C.; Härter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194.
171. (b) Nicolaou, K. C.; Baran, P. S.; Zhong, Y. L.; Choi, H. S.; Yoon, W. H.; He, Y.; Fong, K. C. Angew. Chem. Int. Ed. 1999, 38, 1669.
172. Nicolaou, K. C.; Jung, J. K.; Yoon, W. H.; He, Y.; Zhong, Y. L.; Baran, P. S. Angew. Chem. Int. Ed. 2000, 39, 1829.
173. Koreeda, M.; Luengo, J. I. J. Org. Chem. 1984, 4963, 2081.
174. Hashimoto, S.-i.; Sakata, S.; Sonegawa, M.; Ikegami, S. J. Am. Chem. Soc. 1988, 110, 3670.
175. For a recent review on the gem-disubstituent effect, see: Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735.
176. Deagostino, A. M.; Maddaluno, J.; Mella, M.; Prandi, C.; Venturello, P. J. Chem. Soc., Perkin Trans. 1 1998, 881.