α-hydroxyallylation reaction of carbonyl compounds

Chemical Reviews

Volumn 107, Issue 9, 2007, Pages 3843-3879

  Lombardo, Macro ^a   Trombini, Claudio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLICS; CARBONYLATION; HYDROXYLATION; PHASE TRANSITIONS; STEREOSELECTIVITY;

ALDOL REACTION; ALLYLATION REACTION; CARBONYL COMPOUNDS;

ORGANOMETALLICS;

ALDEHYDE; ALLYL COMPOUND; BORANE DERIVATIVE; BORONIC ACID DERIVATIVE; CHROMIUM; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; INDIUM; METAL; TIN DERIVATIVE; ZIRCONIUM;

CHEMISTRY; HYDROXYLATION; REVIEW;

ALDEHYDES; ALLYL COMPOUNDS; BORANES; BORONIC ACIDS; CHROMIUM; HYDROXYLATION; INDICATORS AND REAGENTS; INDIUM; METALS; TIN COMPOUNDS; ZIRCONIUM;

EID: 35148869059     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr068443u     Document Type: Review

References (250)

1. (a) Yeung, K.-S.; Paterson, I. Chem. Rev. 2005, 105, 4237.
2. (b) Nakata, T. Chem. Rev. 2005, 105, 4314.
3. (c) Inoue, M. Chem. Rev. 2005, 105, 4379.
4. (d) Yeung, S. H.; Kang, S. Y.; Lee, H.-S.; Buglass, A. J. Chem. Rev. 2005, 105, 4537.
5. (e) Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677.
6. (f) Schneider, C. Angew. Chem., Int. Ed. 1998, 37, 1375.
7. (g) Rychnovsky, S. D. Chem, Rev. 1995, 95, 2021.
8. (h) Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041.
9. For recent reviews, see: (a) Rose, E.; Andrioletti, B.; Zrig, S.; Quelquejeu-Etheve, M. Chem. Soc. Rev. 2005, 34, 573.
10. (b) McGarrigle, E. M.; Gilheany, D. G. Chem. Rev. 2005, 105, 1563.
11. (c) Katsuki, T. Transition Met. Org. Synth. 2004, 2, 337.
12. (d) Muniz-Fernandez, K.; Bolm, C. Transition Met. Org. Synth. 2004, 2, 344.
13. (e) Shi, Y. Mod. Oxid. Methods 2004, 51.
14. (f) Kolb, H. C.; Sharpless, K. B. Transition Met. Org. Synth. 2004, 2, 275.
15. (g) Kolb, H. C.; Sharpless, K. B. Transition Met. Org. Synth. 2004, 2, 309.
16. (h) Mehrman, S. J.; Abdel-Magid, A. F.; Maryanoff, C. A.; Medaer, B. P. Top. Organomet. Chem. 2004, 6, 153.
17. (i) Bayer, A. Comp. Asym. Catal. Suppl. 2004, 2, 21.
18. Kubota, K.; Mori, S.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 1998, 120, 1334.
19. Evidence was collected by several authors about the reversibility of the allylation reaction of carbonyl compounds and imines with crotyl metal complexes: (a) Grilli, S.; Martelli, G.; Savoia, D. Eur. J. Org. Chem. 2001, 2917.
20. (b) Jones, P.; Knochel, P. J. Org. Chem. 1999, 64, 186.
21. (c) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766.
22. (d) Benkeser, R. A.; Siklosi, M. P.; Mozdzen, E. C. J. Am. Chem. Soc. 1978, 100, 2134.
23. (d) Barbot, F.; Miginiac, P. J. Organomet. Chem. 1977, 132, 445.
24. Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1982, 21, 555.
25. Koreeda, M.; Tanaka, Y. Tetrahedron Lett. 1987, 28, 143.
26. Hoffmann, R. W.; Kemper, B.; Metternich, R.; Lehmeier, T. Liebigs Ann. Chem. 1985, 2246.
27. Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, p 1.
28. (a) Ahlbrecht, H.; Beyer, U. Synthesis 1999, 365.
29. (b) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282.
30. (c) Crimmins, M. T.; Nantermet, P. G. Org. Prep. Proced. Int. 1993, 25, 43.
31. (a) Seppi, M.; Kalkofen, R.; Reupohl, J.; Froehlich, R.; Hoppe, D. Angew. Chem., Int. Ed. 2004, 43, 1423.
32. (b) Hoppe, D.; Zschage, O. Angew. Chem., Int. Ed. Engl. 1989, 28, 69.
33. Beckmann, E.; Hoppe, D. Synthesis 2005, 217.
34. Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657.
35. (a) Marshall, J. A.; Hinkle, K. J. Org. Chem. 1995, 60, 1920.
36. (b) Hoffmann, R. W.; Kemper, B. Tetrahedron Lett. 1982, 23, 845.
37. For a general discussion about cyclic transition states involved in the allylation/crotylation of carbonyl compounds, see: Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Heathcock, C. H., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol 2, pp 1-53.
38. Evans, D. A.; Andrews, G. C.; Buckwalter, B. J. Am. Chem. Soc. 1974, 96, 5560.
39. Still, W. K.; Macdonald, T. L. J. Am. Chem. Soc. 1974, 96, 5561.
40. Lombardo, M.; Spada, S.; Trombini, C. Eur. J. Org. Chem. 1998, 2361.
41. Fiorelli, C.; Maini, L.; Martelli, G.; Savoia, D.; Zazzetta, C. Tetrahedron 2002, 58, 8679.
42. Hirashita, T.; Kamei, T.; Horie, T.; Yamamura, H.; Kawai, M.; Araki, S. J. Org. Chem. 1999, 64, 172.
43. Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415.
44. Marek, I.; Normant, J. F. In Metal-catalysed cross-coupling reactions; Diederich, F., Stang, P., Eds.; Wiley-VCH: Weinheim, 1998; pp 271-337.
45. Marek, I.; Lefrancois, J.-M.; Normant, J.-F. J. Org. Chem. 1994, 59, 4154.
46. Ferreira, F.; Herse, C.; Riguet, E.; Normant, J.-F. Tetrahedron Lett. 2000, 41, 1733.
47. Yamamoto, Y.; Yatagai, H.; Maruyama, K. J. Org. Chem. 1980, 45, 195.
48. Yamamoto, Y.; Yatagai, H.; Saito, Y. J. Org. Chem. 1984, 49, 1096.
49. Chika, J.; Takei, H. Tetrahedron Lett. 1998, 39, 605.
50. Micalizio, G. C.; Pinchuk, A. N.; Roush, W. R. J. Org. Chem. 2000, 65, 8730.
51. Reetz, M. T. Organotitanium reagents in organic synthesis; Springer-Verlag: Berlin, 1986.
52. Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321.
53. Fürstner, A.; Müller, C. Chem. Commun. 2005, 5583.
54. Cossy, J.; Willis, C.; Bellosta, V.; Saint-Jalmes, L. Synthesis 2002, 951.
55. Castoldi, D.; Caggiano, L.; Panigada, L.; Sharon, O.; Costa, A. M.; Gennari, C. Angew. Chem., Int. Ed. 2005, 44, 588.
56. Hoffmann, R. W.; Kemper, B. Tetrahedron Lett. 1981, 22, 5263.
57. Wuts, P. G. M.; Bigelow, S. S. J. Org. Chem. 1982, 47, 2498.
58. Hoffmann, R. W.; Kemper, B.; Metternich, R.; Lehmeier, T. Liebigs Ann. Chem. 1985, 2246.
59. Hoffmann, R. W.; Polachowski, A. Chem.-Eur. J. 1998, 4, 1724.
60. (a) Yamamoto, Y.; Miyairi, T.; Ohmura, T.; Miyaura, N. J. Org. Chem. 1999, 64, 296.
61. (b) Moriya, T.; Suzuki, A.; Miyaura, N. Tetrahedron Lett. 1995, 36, 1887.
62. Hoffmann, R. W.; Krüger, J.; Brückner, D. New J. Chem. 2001, 25, 102.
63. Hoffmann, R. W.; Metternich, R.; Lanz, J. W. Liebigs Ann. Chem. 1987, 881.
64. Roush, W. R.; Michaelides, M. R.; Tai, D. F.; Lesur, B. M.; Chong, W. K. M.; Harris, D. J. J. Am. Chem. Soc. 1989, 111, 2984.
65. Hoffmann, R. W.; Münster, I. Tetrahedron Lett. 1995, 36, 1431.
66. Yamamoto, Y.; Kurihara, K.; Yamada, A.; Takahashi, M.; Takahashi, Y.; Miyaura, N. Tetrahedron 2003, 59, 537.
67. (a) Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Pure Appl. Chem. 2003, 75, 1263.
68. (b) Ramachandran, P. V. Aldrichim. Acta 2002, 35, 23.
69. (c) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535.
70. Ramachandran, P. V.; Burghardt, T. E.; Reddy, M. V. R. J. Org. Chem. 2005, 70, 2329.
71. Ganesh, P.; Nicholas, K. M. J. Org. Chem. 1997, 62, 1737.
72. Ramachandran, P. V.; Padiya, K. J.; Reddy, M. V. R.; Brown, H. C. J. Fluorine Chem. 2004, 125, 579.
73. Ramachandran, P. V.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2002, 67, 7547.
74. (a) Ramachandran, P. V.; Chandra, J. S.; Prabhudas, B.; Pratihar, D.; Reddy, M. V. R. Org. Biomol. Chem. 2005, 3, 3812.
75. (b) Ramachandran, P. V.; Prabhudas, B.; Pratihar, D.; Chandra, J. S.; Ram, M. V. Tetrahedron Lett. 2003, 44, 3745.
76. Liao, X.; Wu, Y.; De Brabander, J. K. Angew. Chem., Int. Ed. 2003, 42, 1648.
77. Liu, B.; Zhou, W.-S. Org. Lett. 2004, 6, 71.
78. Zhang, Q.; Lu, H.; Richard, C.; Curran, D. P. J. Am. Chem. Soc. 2004, 126, 36.
79. Ramachandran, P. V.; Burghardt, T. E.; Reddy, M. V. R. J. Org. Chem. 2005, 70, 2329.
80. Ahmed, M.; Barrett, A. G. M.; Beall, J. C.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Procopiou, P. A.; Salter, M. M. Tetrahedron 1999, 55, 3219.
81. Barrett, A. G. M.; Beall, J. C.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Salter, M. M. J. Org. Chem. 2000, 65, 6508.
82. Ramachandran, P. V.; Liu, H.; Reddy, M. V. R.; Brown, H. C. Org. Lett. 2003, 5, 3755.
83. Carter, K. D.; Panek, J. S. Org. Lett. 2004, 6, 55. For an alternative approach based on the use of γ-Z-54b,
84. see: Canova, S.; Bellosta, V.; Bigot, A.; Mailliet, P.; Mignani, S.; Cossy, J. Org. Lett., 2007, 9, 145.
85. Ramachandran, P. V.; Burghardt, T. E. Chem.-Eur. J. 2005, 11, 4387.
86. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1996, 61, 2677.
87. Wolf, G.; Würthwein, E. U. Chem. Ber. 1991, 124, 655.
88. Keck, G. E.; Abbott, D. E.; Wiley, M. R. Tetrahedron Lett. 1987, 28, 139.
89. Koreeda, M.; Tanaka, Y. Tetrahedron Lett. 1987, 28, 143.
90. Roush, W. R.; NewcoM, J. S. Org. Lett. 2002, 4, 4739.
91. Zahra, J.; Hennig, L.; Findeisen, M.; Giesa, S.; Welzel, P.; Müller, D.; Sheldrick, W. S. Tetrahedron 2001, 57, 9437.
92. Toshima, K.; Arita, T.; Kato, K.; Tanaka, D.; Matsumura, S. Tetrahedron Lett. 2001, 42, 8873.
93. Abe, K.; Kato, K.; Arai, T.; Rahim, M. A.; Sultana, I.; Matsumura, S.; Toshima, K. Tetrahedron Lett. 2004, 45, 8849.
94. Kadota, I.; Kobayashi, K.; Okano, H.; Asao, N.; Yamamoto, Y. Bull. Soc. Chim. Fr. 1995, 132, 615.
95. Roush, W. R.; VanNieuwenhze, M. S. J. Am. Chem. Soc. 1994, 116, 8536.
96. Micalizio, G. C.; Roush, W. R. Tetrahedron Lett. 1999, 40, 3351.
97. (a) Dubost, C.; Leroy, B.; Markó, I. E.; Tinant, B.; Declercq, J. P.; Bryans, J. Tetrahedron 2004, 60, 7693.
98. (b) Leroy, B.; Markó, I. E. Org. Lett. 2002, 4, 47.
99. Leroy, B.; Markó, I. E. J. Org. Chem. 2002, 67, 8744.
100. (a) Madec, D.; Férézou, J.-P. Tetrahedron Lett. 1997, 38, 6657.
101. (b) Madec, D.; Férézou, J.-P. Tetrahedron Lett. 1997, 38, 6661.
102. Madec, D.; Férézou, J.-P. Eur. J. Org. Chem. 2006, 92.
103. Williams, D. R.; Fultz, M. W. J. Am. Chem. Soc. 2005, 127, 14550.
104. Watrelot, S.; Parrain, J.-L.; Quintard, J.-P. J. Org. Chem. 1994, 59, 7959.
105. (a) Fliegel, F.; Beaudet, I.; Watrelot-Bourdeau, S.; Cornet, N.; Quintard, J.-P. J. Organomet. Chem. 2005, 690, 659.
106. (b) Beaudet, I.; Parrain, J.-L.; Quintard, J.-P. Tetrahedron Lett. 1991, 32, 6333.
107. (c) Marek, I.; Alexakis, A.; Normant, J.-F. Tetrahedron Lett. 1991, 32, 6337.
108. Watrelot-Bourdeau, S.; Parrain, J.-L; Quintard, J.-P. J. Org. Chem. 1997, 62, 8261.
109. Fliegel, F.; Beaudet, I.; Quintard, J.-P. J. Organomet. Chem. 2001, 624, 383.
110. Marshall, R. L.; Young, D. J. Tetrahedron Lett. 1992, 33, 2369.
111. Savall, B. M.; Powell, N. A.; Roush, W. R. Org. Lett. 2001, 3, 3057.
112. Marshall, J. A. Chem. Rev. 1996, 96, 31.
113. (a) Marshall, J. A.; Garofalo, A. W.; Hinkle, K. W. Org. Synth. 2000, 77, 98.
114. (b) Marshall, J. A.; Welmaker, G. S.; Gung, B. W. J. Am. Chem. Soc. 1991, 113, 647.
115. (c) Chan, P. C.-M.; Chong, J. M. J. Org. Chem. 1988, 53, 5594.
116. Marshall, J. A.; Jablonowski, J. A.; Elliott, L. M. J. Org. Chem. 1995, 60, 2662.
117. Marshall, J. A.; Welmaker, G. S. J. Org. Chem. 1992, 57, 7158.
118. Marshall, J. A.; Jablonowski, J. A.; Welmaker, G. S. J. Org. Chem. 1996, 61, 2904.
119. Marshall, J. A.; Schaaf, G.; Nolting, A. Org. Lett. 2005, 7, 5331.
120. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
121. (a) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 105.
122. (b) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 4247.
123. Cossy, J.; Rasamison, C.; Pardo, D. G.; Marshall, J. A. Synlett 2001, 629.
124. (a) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1997, 62, 5989.
125. (b) Marshall, J. A.; Chen, M. J. Org. Chem. 1997, 62, 5996.
126. c) Marshall, J. A.; Jiang, H. J. Org. Chem. 1999, 64, 971.
127. (d) Marshall, J. A.; Jiang, H. J. Nat. Prod. 1999, 62, 1123.
128. Marshall, J. A.; Piettre, A.; Paige, M. A.; Valeriote, F. J. Org. Chem. 2003, 68, 1771.
129. Yamamoto, Y.; Schmid, M. J. Chem. Soc., Chem. Commun. 1989, 1310.
130. (a) Chevallier, F.; Beaudet, I.; Le Grognec, E.; Toupet, L.; Quintard, J.-P. Tetrahedron Lett. 2004, 45, 761.
131. (b) Marshall, J. A.; Gill, K.; Seletsky, B. M. Angew. Chem., Int. Ed. 2000, 39, 953.
132. (a) Park J.-Y.; Kadota, I.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4901.
133. (b) Kadota, I.; Park, J.-Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 841.
134. Park, J.-Y.; Park, C.-H.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 1791.
135. Costa, A.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001.
136. Marshall, J. A.; Gung, W. Y. Tetrahedron Lett. 1988, 29, 3899.
137. Marshall, J. A.; Gung, W. Y. Tetrahedron Lett. 1989, 30, 309.
138. Kadota, I.; Yamamoto, Y. Acc. Chem. Res. 2005, 38, 423.
139. Yamamoto, Y.; Yamada, J.; Kadota, I. Tetrahedron Lett. 1991, 32, 7069.
140. Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597.
141. Yamada, J.; Asano, T.; Kadota, I.; Yamamoto, Y. J. Org. Chem. 1990, 55, 6066.
142. Kadota, I.; Miura, K.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1994, 1953.
143. Inoue, M.; Sasaki, M.; Tachibana, K. J. Org. Chem. 1999, 64, 9416.
144. (a) Kadota, I.; Ueno, H.; Sato, Y.; Yamamoto, Y. Tetrahedron Lett. 2006, 47, 89.
145. (b) Kadota, I.; Ueno, H.; Yamamoto, Y. Tetrahedron Lett. 2003, 44, 8935.
146. (a) Kadota, I.; Nishii, H.; Ishioka, H.; Takamura, H.; Yamamoto, Y. J. Org. Chem. 2006, 71, 4183.
147. (b) Kadota, I.; Takamura, H.; Nishii, H.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9246.
148. Dahanukar, V. H.; Rychnovsky, S. D. J. Org. Chem. 1996, 61, 8317.
149. Fraenkel, G.; Chow, A.; Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 2582.
150. Chan, T. H.; Wang, D. Chem. Rev. 1995, 95, 1279.
151. Agami, C.; Comesse, S.; Kadouri-Puchot, C. J. Org. Chem. 2002, 67, 1496.
152. Ehlinger, E.; Magnus, P. J. Am. Chem. Soc. 1980, 102, 5004.
153. Yamamoto, Y.; Saito, Y.; Maruyama, K. Tetrahedron Lett. 1982, 23, 4597.
154. Tsai, D. J. S.; Matteson, D. S. Tetrahedron Lett. 1981, 22, 2751.
155. Sato, F.; Suzuki, Y.; Sato, M. Tetrahedron Lett. 1982, 23, 4589.
156. Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37.
157. (a) Fleming, I.; Henning, R.; Parker, D. C.; Plant, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1995, 1, 317.
158. (b) Fleming, I.; Sanderson, P. E. J. Tetrahedron Lett. 1987, 28, 4229.
159. (c) Fleming, I.; Henning, R.; Plant, H. J. Chem. Soc., Chem. Commun. 1984, 29.
160. Tamao, K.; Nakajo, E.; Ito, Y. J. Org. Chem. 1987, 52, 957.
161. Roush, W. R.; Grover, P. T.; Lin, X. Tetrahedron 1992, 48, 1981 and references therein.
162. Tinsley, J. M.; Mertz, E. M.; Chong, P. Y.; Rarig, R.-A. F.; Roush, W. R. Org. Lett. 2005, 7, 4245.
163. (a) Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112.
164. (b) Hunt, J. A.; Roush, W. R. Tetrahedron Lett. 1995, 36, 501.
165. (a) Barrett, A. G. M.; Malecha, J. W. J. Chem. Soc., Perkin Trans. 1 1994, 1901.
166. (b) Barrett, A. G. M.; Malecha, J. W. J. Org. Chem. 1991, 56, 5243.
167. Liang, X.; Andersch, J.; Bols, M. J. Chem. Soc., Perkin Trans. 1 2001, 2136.
168. Go, Y. G.; Wang, K. K. Tetrahedron Lett. 1991, 32, 3029.
169. Brown, H. C.; Ramachandran, P. V. J. Organomet. Chem. 1995, 500, 1.
170. Roush, W. R.; Pinchuk, A. N.; Micalizio, G. C. Tetrahedron Lett. 2000, 41, 9413.
171. Heo, J. -N.; Micalizio, G. C.; Roush, W. R. Org. Lett. 2003, 5, 1693.
172. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
173. Kopecky, D. J.; Rychnovsky, S. D. J. Org. Chem. 2000, 65, 191.
174. Roush, W. R.; Dilley, G. J. Synlett 2001, 955.
175. Shotwell, J. B.; Roush, W. R. Org. Lett. 2004, 6, 3865.
176. Lambert, W. T.; Roush, W. R. Org. Lett. 2005, 7, 5501.
177. (a) Mertz, E.; Tinsley, J. M.; Roush, W. R. J. Org. Chem. 2005, 70, 8035.
178. (b) Tinsley, J. M.; Roush, W. R. J. Am. Chem. Soc. 2005, 127, 10818.
179. Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Organomet. Chem. 1985, 292, 311.
180. Keck, G. E.; Romer, D. R. J. Org. Chem. 1993, 58, 6083.
181. Evano, G.; Schaus, J. V.; Panek, J. S. Org. Lett. 2004, 6, 525.
182. Yu, C.-M.; Kim, J.-M.; Shin, M.-S.; Yoon, M.-O. Chem. Commun. 2003, 1744.
183. Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993.
184. Brown, H. C.; Narla, G. J. Org. Chem. 1995, 60, 4686.
185. Flamme, E. M.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 13644.
186. Owen, R. M.; Roush, W. R. Org. Lett. 2005, 7, 3941.
187. Flamme, E. M.; Roush, W. R. Org. Lett. 2005, 7, 1411.
188. Hicks, J. D.; Flamme, E. M.; Roush, W. R. Org. Lett. 2005, 7, 5509.
189. (a) Takai, K. Org. React. 2004, 64, 253.
190. (b) Fürstner, A. Chem. Rev. 1999, 99, 991.
191. (c) Cintas, P. Synthesis 1992, 248.
192. (a) Takai, K.; Nitta, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5263.
193. (b) Marshall, J. A.; Adams, N. D. J. Org. Chem., 2002, 67, 733.
194. (c) Toshima, K.; Jyojima, T.; Yamaguchi, H.; Noguchi, Y.; Yoshida, T.; Murase, H.; Nakata, M.; Matsumura, S. J. Org. Chem., 1997, 62, 3271.
195. (d) Roush, W. R.; Bannister, T. D.; Wendt, M. D.; Jablonowski, J. A.; Scheidt, K. A. J. Org. Chem., 2002, 67, 4275.
196. Takai, K.; Morita, R.; Toratsu, C. Angew. Chem., Int. Ed. 2001, 40, 1116.
197. United States Environmental Protection Agency, Office of Water, Office of Science and Technology, National Recommended Water Quality Criteria, Fact Sheet: May 2005. See: http://www.epa.gov/waterscience/criteria/ 2004-table-fs.htm.
198. Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349.
199. Boeckman, R. K., Jr.; Hudack, R. A., Jr. J. Org. Chem. 1998, 63, 3524.
200. Jung, M.; Groth, U. Synlett 2002, 2015.
201. Groth, U.; Jung, M.; Vogel, T. Chem.-Eur. J. 2005, 11, 3127.
202. Ito, H.; Sato, A.; Taguchi, T. Tetrahedron 2005, 61, 10868.
203. Negishi, E.; Cederbaum, F. K.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829.
204. (a) Ito, H.; Nakamura, T.; Taguchi, T.; Hanzawa, Y. Tetrahedron 1995, 51, 4507.
205. (b) Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 7873.
206. Ito, H.; Taguchi, T. Tetrahedron Lett. 1997, 38, 5829.
207. Sato, A.; Ito, H.; Taguchi, T. J. Org. Chem. 2000, 65, 918.
208. Ito, H.; Kuroi, H.; Ding, H.; Taguchi, T. J. Am. Chem. Soc. 1998, 120, 6623.
209. Sato, A.; Ito, H.; Okada, M.; Nakamura, Y.; Taguchi, T. Tetrahedron Lett. 2005, 46, 8381.
210. Sato, A.; Ito, H.; Taguchi, T. J. Org. Chem. 2005, 70, 709.
211. Kirrmann, A. Bull. Soc. Chim. Fr. 1938, 256.
212. Lombardo, M.; Licciulli, S.; Trombini, C. Pure Appl. Chem. 2004, 76, 657.
213. Neuenschwander, M.; Bigler, P.; Christen, K.; Iseli, R.; Kyburz, R.; Mühle, H. Helv. Chim. Acta 1978, 61, 2047.
214. (a) Lindström, U. L. Chem. Rev. 2002, 102, 2751.
215. (b) Lubineau, A.; Augá, J.; Queneau, Y. Synthesis 1994, 741.
216. Pétrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910.
217. (a) Levoirier, E.; Canac, Y.; Norsikian, S.; Lubineau, A. Carbohydr. Res. 2004, 339, 2737.
218. (b) Tan, K.-T.; Chug, S.-S.; Cheng, H.-S.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 2958.
219. (c) Podlech, J.; Maier, T. C. Synthesis 2003, 633.
220. (d) Li, C.-J. Green Chem. 2002, 4, 1.
221. (e) Li, C. H.; Chan, T. H. Tetrahedron 1999, 55, 11149.
222. (f) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333.
223. Girotti, R.; Lombardo, M.; Morganti, S.; Trombini, C. Chem. Commun. 2001, 2310.
224. Lombardo, M.; Morganti, S.; Trombini, C. J. Org. Chem. 2003, 68, 997.
225. Lombardo, M.; Morganti, S.; d'Ambrosio, F.; Trombini, C. Tetrahedron Lett. 2003, 44, 2823.
226. Lombardo, M.; Girotti, R.; Morganti, S.; Trombini, C. Org. Lett. 2001, 3, 2981.
227. (a) Lombardo, M.; Licciulli, S.; Trombini, C. Tetrahedron Lett. 2003, 44, 9147.
228. (b) Lombardo, M.; Gianotti, K.; Licciulli, S.; Trombini, C. Tetrahedron 2004, 60, 11725.
229. Palmelund, A.; Madsen, R. J. Org. Chem. 2005, 70, 9248.
230. Keinicke, L.; Madsen, R. Org. Biomol. Chem. 2005, 3, 4124.
231. Lombardo, M.; Pasi, F.; Tiberi, C.; Trombini, C. Synthesis 2005, 2609.
232. Lombardo, M.; Pasi, F.; Trombini, C. Eur. J. Org. Chem. 2006, 3061.
233. Lombardo, M.; Capdevila, M. G.; Pasi, F.; Trombini, C. Org. Lett. 2006, 8, 3303.
234. Keinicke, L.; Fristrup, P.; Norrby, P.-O.; Madsen, R. J. Am. Chem. Soc. 2005, 127, 15756.
235. (a) Giri, N.; Petrini, M.; Profeta, R. J. Org. Chem. 2004, 69, 7303.
236. (b) Petrini, M.; Profeta, R.; Righi, P. J. Org. Chem. 2002, 67, 4530.
237. Lombardo, M.; Mosconi, E.; Pasi, F.; Petrini, M.; Trombini, C. J. Org. Chem. 2007, 72, 1834.
238. Petrini, M. Chem. Rev. 2005, 105, 3949.
239. Lombardo, M.; Rispoli, G.; Licciulli, S.; Trombini, C.; Dhavale, D. D. Tetrahedron Lett. 2005, 46, 3789.
240. Lombardo, M.; Morganti, S.; Licciulli, S.; Trombini, C. Synlett 2003, 43.
241. (a) Denmark, S. E.; Fu, J. Chem. Commun. 2003, 167.
242. (b) Denmark, S. E.; Beutner, G. L. J. Am. Chem. Soc. 2003, 125, 7800.
243. Bandini, M.; Cozzi, P. G.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2000, 39, 2327.
244. Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763.
245. Lombardo, M.; Licciulli, S.; Morganti, S.; Trombini, C. Chem. Commun. 2003, 1762.
246. Cutler, A.; Ehnholt, D.; Lennon, P.; Nicholas, K.; Marten, D. F.; Madhavarao, M.; Raghu, S.; Rosan, A.; Rosenblum, M. J. Am. Chem. Soc. 1975, 97, 3149.
247. Jang, S.; Agoston, G. E.; Chen, T.; Cabal, M.-P.; Turos, E. Organometallics 1995, 14, 4697.
248. Hirayama, T.; Oshima, K.; Matsubara, S. Angew. Chem., Int. Ed. 2005, 44, 3293.
249. Gao, X.; Hall, D. G.; Deligny, M.; Favre, A.; Carreaux, F.; Carboni, B. Chem. - Eur. J. 2006, 12, 3132.
250. Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 3059.