Pd-mediated reactions of epoxides

European Journal of Organic Chemistry

Volumn , Issue 25, 2011, Pages 4717-4741

  Muzart, Jacques ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

Addition reactions; Cleavage reactions; Epoxides; Heterogeneous catalysis; Homogeneous catalysis; Isomerization; Palladium

Indexed keywords

EID: 80052014769     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100143     Document Type: Review

References (211)

1. S. N. Lewis, in Oxidation (Ed.:, R. L. Augustine), Dekker, New York, 1969, vol. 1, p. 213-258.
2. R. Hiatt, in: Oxidation (Ed.:, R. L. Augustine), Dekker, New York, 1971, vol. 2, p. 113-140.
3. R. A. Sheldon, J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981, p. 275-288.
4. G. Goor, in: Catalytic Oxidations with Hydrogen Peroxide (Ed.:, G. Strukul), Kluwer Academic, Dordrecht, 1992, p. 13-43.
5. Y. Ogata, Y. Sawaki, in: Organic Syntheses by Oxidation with Metal Compounds (Eds.:, W. J. Miss, C. R. H. I. De Jonge,), Plenum Press, New York, 1986, p. 846-852.
6. R. C. Larock, Comprehensive Organic Transformations, VCH Publishers, New York, 1989, p. 456-461.
7. J. Muzart, J. Mol. Catal. A 2007, 276, 62-72.
8. J. Gorzynski Smith, Synthesis 1984, 629-656.
9. E. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421-431.
10. S. K. Taylor, Tetrahedron 2000, 56, 1149-1163.
11. M. Pineschi, Eur. J. Org. Chem. 2006, 4979-4988.
12. C. Schneider, Synthesis 2006, 3919-3944.
13. S. H. Krake, S. C. Bergmeier, Tetrahedron 2010, 66, 7337-7360.
14. E. Thiery, J. Le Bras, J. Muzart, Eur. J. Org. Chem. 2009, 961-985.
15. For a recent reference, see:, S. Yakabe, Synth. Commun. 2010, 40, 1339-1344.
16. S. Fukuoka, M. Ryang, S. Tsutsumi, J. Org. Chem. 1970, 35, 3184-3186.
17. D. Milstein, O. Buchman, J. Blum, Tetrahedron Lett. 1974, 15, 2257-2260.
18. B. C. Ranu, U. Jana, J. Org. Chem. 1998, 63, 8212-8216.
19. A. M. Anderson, J. M. Blazek, P. Garg, B. J. Payne, R. S. Mohan, Tetrahedron Lett. 2000, 41, 1527-1530.
20. K. A. Bhatia, K. J. Eash, N. M. Leonard, M. C. Oswald, R. S. Mohan, Tetrahedron Lett. 2001, 42, 8129-8132.
21. M. W. C. Robinson, K. S. Pillinger, I. Mabbett, D. A. Timms, A. E. Graham, Tetrahedron 2010, 66, 8377-8382.
22. D. Milstein, O. Buchman, J. Blum, J. Org. Chem. 1977, 42, 2299-2308.
23. Y. D. Vankar, N. C. Chaudhuri, S. P. Singh, Synth. Commun. 1986, 16, 1621-1626.
24. S. Kulasegaram, R. J. Kulawiec, J. Org. Chem. 1994, 59, 7195-7196.
25. S. Kulasegaram, R. J. Kulawiec, J. Org. Chem. 1997, 62, 6547-6561.
26. T. Mandai, T. Matsumoto, J. Tsuji, S. Saito, Tetrahedron Lett. 1993, 34, 2513-2516.
27. 3 mixtures:, C. Amatore, E. Carré, A. Jutand, M. A. M'Barki, G. Meyer, Organometallics 1995, 14, 5605-5614.
28. J. Wu, R. G. Bergman, J. Am. Chem. Soc. 1989, 111, 7628-7630.
29. D. Milstein, J. C. Calabrese, J. Am. Chem. Soc. 1982, 104, 3773-3774.
30. M. J. Calhorda, A. M. Galvão, C. Ünaleroglu, A. A. Zlota, F. Frolow, D. Milstein, Organometallics 1993, 12, 3316-3325.
31. The enolate connectivity to palladium is strongly dependent on the natures of the ligands and their geometries around the palladium:, J. Vicente, A. Arcas, J. M. Fernández-Hernández, D. Bautista, Organometallics 2004, 23, 3398-3416.
32. S. Kulasegaram, R. J. Kulawiec, Tetrahedron 1998, 54, 1361-1374.
33. R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, London, 1985.
34. The Mizoroki-Heck Reaction (Ed.:, M. Oestreich), Wiley, Chichester, 2009.
35. J. Muzart, Tetrahedron 2003, 59, 5789-5816.
36. B. M. Stoltz, Chem. Lett. 2004, 33, 362-367.
37. B.-Z. Zhan, A. Thompson, Tetrahedron 2004, 60, 2917-2935.
38. T. Nishimura, S. Uemura, Synlett 2004, 201-216.
39. S. S. Stahl, Angew. Chem. Int. Ed. 2004, 43, 3400-3420.
40. M. E. Sigman, D. R. Jensen, Acc. Chem. Res. 2006, 39, 221-229.
41. J. March, Advanced Organic Chemistry, McGraw-Hill, New York, 2nd ed., 1977, p. 896-903.
42. J. García-Fortanet, J. R. Debergh, J. K. De Brabander, Org. Lett. 2005, 7, 685-688.
43. J.-H. Kim, R. J. Kulawiec, J. Org. Chem. 1996, 61, 7656-7657.
44. C. Amatore, E. Carré, A. Jutand, M. A. M'Barki, Organometallics 1992, 11, 3009-3013.
45. J. Vicente, J. A. Abad, M.-T. Chicote, M.-D. Abrisqueta, J.-A. Lorca, M. C. Ramírez de Arellano, Organometallics 1998, 17, 1564-1568.
46. J. Muzart, Eur. J. Org. Chem. 2010, 3779-3790.
47. J.-H. Kim, R. J. Kulawiec, Tetrahedron Lett. 1998, 39, 3107-3110.
48. R. H. Sommerlade, Y. Richter, WO 2006005682 A2 20060119, 2006.
49. Chem. Abstr. 144, 150225.
50. G. W. Amarante, F. Coelho, Tetrahedron 2010, 66, 6749-6753.
51. [19a,19c-19f]
52. II active species, see
53. K. M. Gligorich, M. S. Sigman, Angew. Chem. Int. Ed. 2006, 45, 6612-6615.
54. J. Muzart, Chem. Asian J. 2006, 1, 508-515.
55. K. M. Gligorich, M. S. Sigman, Chem. Commun. 2009, 3854-3867.
56. 2 remain a matter of debate, and could be ligand-dependent
57. [30]
58. M. M. Konnick, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 5753-5762.
59. C. Chevrin, J. Le Bras, F. Hénin, J. Muzart, Synthesis 2005, 2615-2618.
60. E. Thiery, C. Chevrin, J. Le Bras, D. Harakat, J. Muzart, J. Org. Chem. 2007, 72, 1859-1862.
61. J. Wahlen, D. E. De Vos, P. A. Jacobs, Org. Lett. 2003, 5, 1777-178.
62. S. Araki, T. Kamei, T. Hirashita, H. Yamamura, M. Kawai, Org. Lett. 2000, 2, 847-849.
63. N. Jiang, Q. Hu, C. S. Reid, Y. Lu, C.-J. Li, Chem. Commun. 2003, 2318-2319.
64. 3, see:, B. C. Ranu, U. Jana, J. Org. Chem. 1998, 63, 8212-8216.
65. P. Sinha, S. Roy, Organometallics 2004, 23, 67-71.
66. M. Banerjee, U. K. Roy, P. Sinha, S. Roy, J. Organomet. Chem. 2005, 690, 1422-1428.
67. U. K. Roy, S. Roy, Tetrahedron 2006, 62, 678-683.
68. J. Muzart, A. Riahi, J. Organomet. Chem. 1992, 433, 323-336.
69. A phenonium ion has previously been proposed as an intermediate to explain the formation of the threo-iodohydrin silyl ether and diphenylacetaldehyde from the cleavage of (E)- and (Z)-stilbene oxides with TMSI:, M. R. Detty, M. D. Seidler, Tetrahedron Lett. 1982, 23, 2543-2546.
70. T. F. Blackburn, J. Schwartz, J. Chem. Soc., Chem. Commun. 1977, 157-158 for a corrigendum, see:, T. F. Blackburn, J. Schwartz, J. Chem. Soc., Chem. Commun. 1977, 632.
71. For the plausible decomposition of diphenylacetaldehyde into acetophenone under metal catalysis conditions, see
72. S. Kobayashi, S. Tobinaga, Chem. Pharm. Bull. 1991, 39, 3025-3029.
73. J. Muzart, A. N'Aït Ajjou, New J. Chem. 1994, 18, 731-736.
74. N. Srinivas, V. Radaha Rani, S. J. Kulkarni, K. V. Raghavan, J. Mol. Catal. A 2002, 179, 221-231.
75. A. Roloff, Chimia 1985, 39, 392-393.
76. M. Tanaka, M. Koyanagi, T. Kobayashi, Tetrahedron Lett. 1981, 22, 3875-3878.
77. [45]
78. J. Prandi, J. L. Namy, G. Menoret, H. B. Kagan, J. Organomet. Chem. 1985, 285, 449-460.
79. Y. D. Vankar, S. P. Singh, Chem. Lett. 1986, 1939-1942.
80. E. Mincione, G. Ortaggi, A. Sirna, J. Org. Chem. 1979, 44, 1569-1570.
81. A. Behr, U. Kanne, J. Organomet. Chem. 1986, 309, 215-223.
82. K. Imi, N. Yanagihara, K. Utimoto, J. Org. Chem. 1987, 52, 1013-1016.
83. K. Okuma, K. Ikari, Fukuoka Daigaku Rigaku Shuho 1996, 26, 57-62. Chem. Abstr. 125, 58221.
84. J. A. Luján-Montelongo, A. Vázquez-Sánchez, J. G. Úvila-Zárraga, Heterocycles 2009, 78, 1955-1976.
85. J. A. Luján-Montelongo, J. G. Úvila-Zárraga, Tetrahedron Lett. 2010, 51, 2232-2236.
86. M. Suzuki, A. Watanabe, R. Noyori, J. Am. Chem. Soc. 1980, 102, 2095-2096.
87. M. Suzuki, A. Watanabe, R. Noyori, Recl. Trav. Chim. Pays-Bas 1988, 107, 230-236.
88. T. Lukac, M. Soukup, E. Widmer, Eur. Pat. Appl. EP 133711, 1985.
89. Chem. Abstr. 103, 104604.
90. S. Sugiura, A. Hasato, S. Kurozumi, Jpn. Kokai Tokkyo Koho JP 85-269482, 1987.
91. Chem. Abstr. 108, 186212.
92. D. Desmaële, J. d'Angelo, J. Org. Chem. 1994, 59, 2292-2303.
93. A. Svennebring, N. Garg, P. Nilsson, A. Hallberg, M. Larhed, J. Org. Chem. 2005, 70, 4720-4725.
94. M. Horikawa, Y. Nakajima, Y. Ohfune, Synlett 1997, 253-254.
95. N. Afza, A. Malik, W. Voelter, J. Chem. Soc. Perkin Trans. 1 1983, 1349-1351.
96. B. M. Choudary, S. S. Rani, M. L. Kantam, Synth. Commun. 1990, 20, 2313-2317.
97. T. Hirao, N. Yamada, Y. Ohshiro, T. Agawa, Chem. Lett. 1982, 1997-2000.
98. [25]
99. T. Hirao, T. Murakami, M. Ohno, Y. Ohshiro, Chem. Lett. 1991, 299-302.
100. 0 have also been reported, but according to the proposed mechanism, the reaction at the level of the oxirane moiety did not involve palladium:, R. Tamura, M. Kato, K. Saegusa, D. Oda, T. Egawa, T. Yamamoto, J. Org. Chem. 1987, 52, 1640-1642.
101. Y. D. Vankar, K. Shah, A. Bawa, S. P. Singh, Tetrahedron 1991, 47, 8883-8906.
102. J. March, Advanced Organic Chemistry, Wiley, New York, 2nd ed., 1987, p. 808-809.
103. M. Lenarda, R. Ros, O. Traverso, W. D. Pitts, W. H. Baddley, M. Graziani, Inorg. Chem. 1977, 16, 3178-3182.
104. R. B. Osborne, J. A. Ibers, J. Organomet. Chem. 1982, 232, 371-385.
105. J. Kjellgren, J. Aydin, O. A. Wallner, I. V. Saltanova, K. J. Szabõ, Chem. Eur. J. 2005, 11, 5260-5268.
106. T. Takahashi, H. Kataoka, J. Tsuji, J. Am. Chem. Soc. 1983, 105, 147-149.
107. J. Lukas, S. Coren, J. E. Blom, J. Chem. Soc. C 1969, 1303-1304.
108. J. Muzart, J. P. Pete, Bull. Soc. Chim. Fr. II 1984, 56-58.
109. J. E. Baldwin, J. Chem. Soc., Chem. Commun. 1976, 734-736.
110. S. Ma, S. Zhao, J. Am. Chem. Soc. 1999, 121, 7943-7944.
111. For reactions summarized in Scheme 13, paths d-g, see
112. J. Tsuji, Palladium Reagents and Catalysts, Innovations in Organic Synthesis, Wiley, Chichester, 1995, p. 376-377.
113. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2944.
114. C. Courillon, S. Thorimbert, M. Malacria, in: Handbook of Organopalladium Chemistry for Organic Synthesis Wiley, Hoboken, 2002, vol. 2, p. 1795-1810.
115. C. Courillon, S. Thorimbert, M. Malacria, C. R. Chim. 2004, 7, 797-807.
116. st Century, Wiley, Chichester, 2004, p. 434-475.
117. J. Muzart, J. Mol. Catal. A 2010, 319, 1-29.
118. For reactions summarized in Scheme 13, path h, see:, S. Araki, K. Kameda, J. Tanaka, T. Hirashita, H. Yamamura, M. Kawai, J. Org. Chem. 2001, 66, 7919-7921.
119. J. Muzart, Tetrahedron 2005, 61, 4179-4212.
120. B. M. Trost, Acc. Chem. Res. 1980, 13, 385-393.
121. B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422.
122. [78b-78d]
123. Y. Nakatani, M. Sugiyama, C. Honbô, Agric. Biol. Chem. 1975, 39, 2431-2432.
124. G. Visentin, O. Piccolo, G. Consiglio, J. Mol. Catal. 1990, 61, L1-L5.
125. S. Achab, J.-P. Cosson, B. C. Das, J. Chem. Soc., Chem. Commun. 1984, 1040-1041.
126. S. Achab, B. C. Das, J. Chem. Soc. Perkin Trans. 1 1990, 2863-2873.
127. V. Fauchet, B. Arreguy-San Miguel, M. Taran, B. Delmond, Synth. Commun. 1999, 29, 3673-3684.
128. [16,88]
129. M. Suzuki, Y. Oda, R. Noyori, J. Am. Chem. Soc. 1979, 101, 1623-1625.
130. T. Minami, M. Hanaoka, Tetrahedron Lett. 1994, 35, 9425-9428.
131. B. M. Trost, Tetrahedron 1977, 33, 2615-2649.
132. B. M. Trost, P. J. Metzner, J. Am. Chem. Soc. 1980, 102, 3572-3577.
133. D. R. Chrisope, P. Beak, W. H. Saunders, J. Am. Chem. Soc. 1988, 110, 230-238.
134. T. Tsuda, M. Tokai, T. Ishida, T. Saegusa, J. Org. Chem. 1986, 51, 5216-5221.
135. B. M. Trost, S. R. Angle, J. Am. Chem. Soc. 1985, 107, 6123-6124.
136. 0 catalysts, carboxylic acids frequently act as nucleophiles towards vinyl epoxides
137. [92]
138. D. R. Deardorff, D. C. Myles, K. D. MacFerrin, Tetrahedron Lett. 1985, 26, 5615-5618.
139. T. Takahashi, H. Tanaka, Y. Hirai, T. Doi, H. Yamada, T. Shiraki, Y. Sugiura, Angew. Chem. Int. Ed. Engl. 1993, 32, 1657-1659.
140. M. G. Banwell, N. Haddad, T. Hudlicky, T. C. Nugent, M. F. Mackay, S. L. Richards, J. Chem. Soc. Perkin Trans. 1 1997, 1779-1791.
141. 3 or diphosphane) firstly requires the dissociation of one L
142. R. H. Crabtree, The Organometallic Chemistry of the Transition Metals, John Wiley & Sons, New York, 2nd ed., 1994, p. 151-153.
143. A. Gillie, J. K. Stille, J. Am. Chem. Soc. 1980, 102, 4933-4941.
144. A. Moravskiy, J. K. Stille, J. Am. Chem. Soc. 1981, 103, 4182-4186.
145. For a review, using computational approaches, on the influence of the ligand properties on the reactivity and selectivity, see:, V. P. Ananikov, D. G. Musaev, K. Morokuma, J. Mol. Catal. A 2010, 324, 104-119.
146. A. T. Menyailo, M. V. Pospelov, N. N. Kirilash, I. M. Krikun, Neftekhimiya 1981, 21, 681-683.
147. Chem. Abstr., 96, 68268.
148. [91]
149. J.-E. Bäckvall, S. K. Juntunen, J. Org. Chem. 1988, 53, 2398-2400.
150. M. M. Kabat, L. M. Garofalo, A. R. Daniewski, S. D. Hutchings, W. Liu, M. Okabe, R. Radinov, Y. Zhou, J. Org. Chem. 2001, 66, 6141-6150.
151. A. R. Daniewski, L. M. Garofalo, S. D. Hutchings, M. M. Kabat, W. Liu, M. Okabe, R. Radinov, G. P. Yiannikouros, J. Org. Chem. 2002, 67,1580-1587.
152. J. H. Rigby, B. Bazin, J. H. Meyer, F. Mohammadi, Org. Lett. 2002, 4, 799-801.
153. P. G. Andersson, S. Schab, Organometallics 1995, 14, 1-2.
154. J. M. Takacs, E. C. Lawson, F. Clement, J. Am. Chem. Soc. 1997, 119, 5956-5957.
155. B. M. Trost, M. A. Ceschi, B. König, Angew. Chem. Int. Ed. Engl. 1997, 36, 1486-1489.
156. D. R. Boyd, N. D. Sharma, C. R. O'Dowd, F. Hempenstall, Chem. Commun. 2000, 2151-2152.
157. D. R. Boyd, N. D. Sharma, N. M. Llamas, C. R. O'Dowd, C. C. R. Allen, Org. Biomol. Chem. 2006, 4, 2208-2217.
158. D. R. Boyd, N. D. Sharma, N. M. Llamas, C. R. O'Dowd, C. C. R. Allen, Org. Biomol. Chem. 2007, 5, 2267-2273.
159. F. Gilloir, M. Malacria, Tetrahedron Lett. 1992, 33, 3859-3862.
160. A. G. Brook, Acc. Chem. Res. 1974, 7, 77-84.
161. F. Le Bideau, F. Gilloir, Y. Nilsson, C. Aubert, M. Malacria, Tetrahedron Lett. 1995, 36, 1641-1644.
162. F. Le Bideau, F. Gilloir, Y. Nilsson, C. Aubert, M. Malacria, Tetrahedron 1996, 52, 7487-7510.
163. F. Le Bideau, C. Aubert, M. Malacria, Tetrahedron: Asymmetry 1995, 6, 697-700.
164. F. Le Bideau, M. Malacria, Phosphorus Sulfur Silicon Relat. Elem. 1995, 107, 275-277.
165. C. Courillon, R. Le Fol, E. Vandendris, M. Malacria, Tetrahedron Lett. 1997, 38, 5493-5496.
166. J.-C. Marié, C. Courillon, M. Malacria, Synlett 2002, 553-556.
167. C. Courillon, J.-C. Marié, M. Malacria, Tetrahedron 2003, 59, 9759-9766.
168. F. Marion, R. Le Fol, C. Courillon, M. Malacria, Synlett 2001, 138-140.
169. F. Marion, S. Calvet, C. Courillon, M. Malacria, Tetrahedron Lett. 2002, 43, 3369-3371.
170. F. Marion, S. Calvet, J.-C. Marié, C. Courillon, M. Malacria, Eur. J. Org. Chem. 2006, 453-462.
171. M. Hentemann, P. L. Fuchs, Tetrahedron Lett. 1999, 40, 2699-2702.
172. K. Yamamoto, C. H. Heathcock, Org. Lett. 2000, 2, 1709-1712.
173. A. G. Myers, D. R. Siegel, D. J. Buzard, M. G. Charest, Org. Lett. 2001, 3, 2923-2926.
174. R. C. Larock, S. J. Ilkka, Tetrahedron Lett. 1986, 27, 2211-2214.
175. 2:, G. D. Daves Jr., Acc. Chem. Res. 1990, 23, 201-206. A syn-β-OAc elimination from a cationic palladium complex has, however, been proposed
176. H. Ohmiya, Y. Makida, T. Tanaka, M. Sawamura, J. Am. Chem. Soc. 2008, 130, 17276-17277.
177. H. Ohmiya, Y. Makida, D. Li, M. Tanabe, M. Sawamura, J. Am. Chem. Soc. 2010, 132, 879-889.
178. R. C. Larock, S. Ding, J. Org. Chem. 1993, 58, 804-806.
179. R. C. Larock, U. S. 5401888 A 19950328 (1995).
180. Chem. Abstr. 123, 8812.
181. N. Miyaura, Y. Tanabe, H. Suginome, A. Suzuki, J. Organomet. Chem. 1982, 233, C13-C16.
182. A. M. Echavarren, D. R. Tueting, J. K. Stille, J. Am. Chem. Soc. 1988, 110, 4039-4041.
183. D. R. Tueting, A. M. Echavarren, J. K. Stille, Tetrahedron 1989, 45, 979-992.
184. A. M. Castano, M. Mendez, M. Ruano, A. M. Echavarren, J. Org. Chem. 2001, 66, 589-593.
185. A. Hirai, X.-Q. Yu, T. Tonooka, M. Miyashita, Chem. Commun. 2003, 2482-2483.
186. [73]
187. R. C. Larock, W. Y. Leung, J. Org. Chem. 1990, 55, 6244-6245.
188. E. Keinan, M. Sahai, I. Kirson, J. Org. Chem. 1983, 48, 2550-2555.
189. B. M. Trost, T. R. Verhoeven, J. M. Fortunak, Tetrahedron Lett. 1979, 20, 2301-2304.
190. B. M. Trost, T. R. Verhoeven, J. Am. Chem. Soc. 1980, 102, 4730-4743.
191. I. Minami, M. Yuhara, H. Watanabe, J. Tsuji, J. Organomet. Chem. 1987, 334, 225-242.
192. I. Minami, M. Yuhara, J. Tsuji, Tetrahedron Lett. 1987, 28, 629-632.
193. M. Yoshida, Y. Morishita, M. Ihara, Tetrahedron Lett. 2005, 46, 3669-3672.
194. M. E. Piotti, H. Alper, J. Org. Chem. 1997, 62, 8484-8489.
195. J. G. Knight, S. W. Ainge, C. A. Baxter, T. P. Eastman, S. J. Harwood, J. Chem. Soc. Perkin Trans. 1 2000, 3188-3190.
196. H. Kleijn, J. Meijer, G. C. Overbeek, P. J. R. Vermeer, Recl. Trav. Chim. Pays-Bas 1982, 101, 97-101.
197. J. Kjellgren, H. Sundén, K. J. Szabõ, J. Am. Chem. Soc. 2005, 127, 1787-1796.
198. M. Yoshida, H. Ueda, M. Ihara, Tetrahedron Lett. 2005, 46, 6705-6708.
199. M. Yoshida, M. Hayashi, K. Shishido, Org. Lett. 2007, 9, 1643-1646.
200. For reviews, see:, J. Tsuji, T. Mandai, Angew. Chem. Int. Ed. Engl. 1995, 34, 2589-2612.
201. C. Bruneau, C. Darcel, P. H. Dixneuf, Curr. Org. Chem. 1997, 1, 197-218.
202. P. Pale, P. Bertus, Tetrahedron Lett. 1996, 37, 2019-2022.
203. R. S. Reddy, S. Iguchi, S. Kobayashi, M. Hirama, Tetrahedron Lett. 1996, 37, 9335-9336.
204. P. Pale, J. Chuche, Eur. J. Org. Chem. 2000, 1019-1025.
205. N. Della Ca', F. Campanini, B. Gabriele, G. Salerno, C. Massera, M. Costa, Adv. Synth. Catal. 2009, 351, 2423-2432.
206. T. Tabuchi, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 5237-5240.
207. J. M. Aurrecoechea, W. H. Okamura, Tetrahedron Lett. 1987, 28, 4947-4950.
208. W. H. Okamura, J. M. Aurrecoechea, R. A. Gibbs, A. W. Norman, J. Org. Chem. 1989, 54, 4072-4083.
209. J. D. Enas, J. A. Palenzuela, W. H. Okamura, J. Am. Chem. Soc. 1991, 113, 1355-1363.
210. J. D. Enas, G. Y. Shen, W. H. Okamura, J. Am. Chem. Soc. 1991, 113, 3873-3881.
211. J. M. Aurrecoechea, M. Solay-Ispizua, Heterocycles 1994, 37, 223-226.