Methods for the cleavage of allylic and propargylic C-N bonds in amines and amides - Selected alternative applications of the 1,3-hydrogèn shift

European Journal of Organic Chemistry

Volumn , Issue 18, 2005, Pages 3855-3873

  Escoubet, Stéphanie ^a   Gastaldi, Stéphane ^a   Bertrand, Michèle ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Amides; Amines; Cleavage reactions; Hydrogen transfer; Nucleophilic substitution; Synthetic methods

Indexed keywords

EID: 24944579952     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500204     Document Type: Short Survey

References (182)

1. a) T. Greene, P. G. Wuts, Protective Groups in Organic Syntheses, 3rd ed., Wiley, New York, 1999;
2. b) P. J. Kocienski, Protecting Groups, Thieme, Stuttgart, 1994;
3. c) F. Guibé, Tetrahedron 1997, 53, 13509-13556.
4. a) M. Rivière, A. Lattes, Bull. Soc. Chim. Fr. 1968, 4430-4435;
5. b) C. C. Price, W. H. Snyder, Tetrahedron Lett. 1962, 69-73.
6. a) R. Gigg, R. Conant, Carbohydr. Chem. 1982, 100, C5-C9, and references cited therein;
7. b) R. Gigg, R. Conant, J. Carbohydr. Chem. 1983, 1, 331-336;
8. c) J. Hine, S.-M. Linden, A. Wang, V. Thiagarajan, J. Org. Chem. 1980, 45, 2821-2825;
9. d) J. Sauer, H. Prahl, Chem. Ber. 1969, 102, 1917-1927.
10. a) J. A. Montgomery, H. J. Thomas, J. Org. Chem. 1965, 30, 3235-3236;
11. b) K. Minamoto, Y. Fujiki, N. Shiomi, Y. Uda, T. Sasaki, J. Chem. Soc., Perkin Trans. 1 1985, 2337-2346.
12. L. Schmitt, C. A. Caperelli, Nucleosides Nucleotides 1997, 2165-2192.
13. L. I. Brutko, P. S. Massagetov, L. M. Utkin, Chem. Nat. Compd. (Engl. Trans.) 1966, 2, 362.
14. a) J. R. Piper, G. S. McCaleb, J. A. Montgomery, J. Heterocycl. Chem. 1987, 24, 279-282 and references cited therein;
15. b) D. A. Ben-Efraim, Tetrahedron 1973, 29, 4111-4125.
16. A. J. Hubert, J. Chem. Soc. C 1968, 2048-2050.
17. G. Y. Kondrat'eva, Y. S. Dol'skaya, Izv. Akad. Nauk SSSR Ser. Khim. 1967, 2045-2048
18. (Chem. Abstr. 68:29199).
19. A. Hattori, H. Hattori, K. Tanabe, J. Catal. 1980, 65, 245-252.
20. a) A. G. M. Barrett, M. A. Seefeld, Tetrahedron 1993, 49, 7857-7870;
21. b) J. J. Eisch, J. H. Shah, J. Org. Chem. 1991, 56, 2955-2957;
22. c) It should be noted that the metalation of secondary allylamines with nBuLi or tBuLi in diethyl ether results in vinyllithiated dianions, see: J. Barluenga, R. Gonzalez, F. J. Fananas, Tetrahedron Lett. 1992, 33, 7573-7574.
23. P. Beak, B. Lee, J. Org. Chem. 1989, 54, 458-464.
24. See also: a) L. E. Fisher, J. M. Muchowski, R. D. Clark, J. Org. Chem. 1992, 57, 2700-2705;
25. b) P. Ribéreau, M. Delamare, S. Célanire, G. Quéguiner, Tetrahedron Lett. 2001, 42, 3571-3573.
26. For the cleavage of the crotyl group (20% yield), in the (Z)-benzylbut-2-enylcarbamic acid tBu ester see: 〈J. C. Anderson, D. C. Siddons, S. C. Smith, M. E. Swarbrick, J. Chem. Soc., Chem. Commun. 1995, 1835-1836.
27. A. N. Tischler, M. H. Tischler, Tetrahedron Lett. 1978, 3407-3410.
28. G. A. Weisenburger, P. Beak, J. Am. Chem. Soc. 1996, 118, 12218-12219.
29. a) D. J. Pippel, G. A. Weisenburger, S. R. Wilson, P. Beak, Angew. Chem. Int. Ed. 1998, 37, 2522-2523;
30. b) Y. S. Park, G. A. Weisenburger, P. Beak, J. Am. Chem. Soc. 1997, 119, 10537-10538.
31. H. Ahlbrecht, C. Vonderheid, Synthesis 1975, 512-515.
32. For an example of unwanted cleavage of N-farnesyl lactams upon treatment with LDA, see: Y. Du, D. F. Wiemer, J. Org. Chem. 2002, 67, 5709-5717.
33. B. M. Novak, J. T. Cafmeyer, J. Am. Chem. Soc. 2001, 123, 11083-11084.
34. a) S. Krompiec, M. Pigulla, M. Krompiec, S. Baj, J. Mrowiec-Bialon, J. Kasperczyk, Tetrahedron Lett. 2004, 45, 5257-5261;
35. b) S. Krompiec, M. Pigulla, W. Szczepankiewicz, T. Bieg, N. Kuznik, K. Leszczynska-Sejda, M. Kubicki, T. Borowiak, Tetrahedron Lett. 2001, 42, 7095-7098;
36. c) S. Krompiec, M. Pigulla, T. Bieg, W. Szczepankiewicz, N. Kuznik, M. Krompiec, M. Kubicki, J. Mol. Catal. A: Chem. 2002, 189, 169-185.
37. R. Sunberg, G. S. Hamilton, J. P. Laurino, J. Org. Chem. 1988, 53, 976-983.
38. J. K. Stille, Y. Becker, J. Org. Chem. 1980, 45, 2139-2145.
39. G. Dominguez, L. Casarrubios, J. Rodriguez-Noriega, J. Pérez-Castells, Helv. Chim. Acta 2002, 85, 2856-2861.
40. H. Kumobayashi, S. Akutagawa, S. Otsuka, J. Am. Chem. Soc. 1978, 100, 3949-3950.
41. M. Onishi, S. Oishi, M. Sakaguchi, I. Takaki, K. Hiraki, Bull. Chem. Soc. Jpn. 1986, 59, 3925-3930.
42. a) B. Alcaide, P. Almendros, J. M. Alonso, M. F. Aly, Org. Lett. 2001, 3, 3781-3784;
43. b) B. Alcaide, P. Almendros, J. M. Alonso, Chem. Eur. J. 2003, 9, 5793-5799;
44. c) B. Alcaide, P. Almendros, J. M. Alonso, A. Luna, Synthesis 2005, 668-672.
45. S. Yang, W. A. Denny, J. Org. Chem. 2002, 67, 8958-8961.
46. C. Cadot, P. I. Dalko, J. Cossy, Tetrahedron Lett. 2002, 43, 1839-1842.
47. B. Alcaide, P. Almendros, J. M. Alonso, Tetrahedron Lett. 2003, 44, 8693-8695.
48. T. Fukuyama, A. A. Laird, C. A. Schmidt, Tetrahedron Lett. 1984, 25, 4709-4712.
49. B. R. McNaughton, K. M. Bucholtz, A. Camaano-Moure. B. L. Miller, Org. Lett. 2005, 7, 733-736.
50. a) For a review on the interference of double-bond migration with the metathesis reaction see: B. Schmidt, Eur. J. Org. Chem. 2004, 1865-1880;
51. b) B. Schimdt, Eur. J. Org. Chem. 2003, 816-819;
52. c) B. Schimdt, J. Org. Chem. 2004, 69, 7672-7687.
53. For discussions about the mechanism of alkene isomerization using Grubbs-type catalysts see: C. D. Edlin, J. Faulkner, D. Fengas, C. K. Knight, J. Parker, I. Preece, P. Quayle, S. N. Richards, Synlett 2005, 572-576 and references cited therein.
54. C. Bressy, C. Menant, O. Piva, Synlett 2005, 577-582.
55. a) B. Moreau, S. Lavielle, A. Marquet, Tetrahedron Lett. 1977, 2591-2594;
56. b) B. C. Laguzza, B. Ganem, Tetrahedron Lett. 1981, 22, 1483-1486;
57. c) J. M. Hawkins, T. A. Lewis, J. Org. Chem. 1994, 59, 649-652.
58. E. J. Corey, J. W. Suggs, J. Org. Chem. 1973, 38, 3224.
59. M. Dufour, J.-C. Gramain, H.-P. Husson, M.-E. Sinibaldi, Y. Troin, Heterocycles 1990, 31, 1477-1484.
60. a) S.-G. Davies, C. J. R. Hedgecock, J. M. McKenna, Tetrahedron: Asymmetry 1995, 6, 2507-2510.
61. For related examples see also: b) S. G. Davies, D. R. Fenwick, O. Ichihara, Tetrahedron: Asymmetry 1997, 8, 3387-3391;
62. c) S. G. Davies, C. J. R. Hedgecock, J. M. McKenna, Tetrahedron: Asymmetry 1995, 6, 827-830;
63. d) S. G. Davies, C. A. P. Smethurst, A. D. Smith, G. D. Smyth, Tetrahedron: Asymmetry 2000, 11, 2437-2441.
64. For additional examples see: a) S. D. Bull, S. G. Davies, A. D. Smith, Tetrahedron: Asymmetry 2001, 12, 2941-2945;
65. b) J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, N. J. Taylor, Tetrahedron: Asymmetry 1995, 6, 409-416;
66. c) A. Warm, Heterocycles 1992, 34, 2263-2267;
67. d) G. Benz, Liehigs Ann. Chem. 1984, 1424-1433;
68. e) D. Enders, C. R. Thomas, G. Raabe, J. Runsink, Helv. Chim. Acta 1998, 81, 1329-1336;
69. f) R. H. Furneaux, G. Limberg, P. C. Tyler, V. L. Schramm, Tetrahedron 1997, 53, 2915-2930.
70. V. H. Lillelund, H. Liu, X. Liang, H. Sohoel, M. Bols, Org. Biomol. Chem. 2003, 1, 282-287.
71. P. B. Alper, M. Hendrix, P. Sears, C.-H. Wong, J. Am. Chem. Soc. 1998, 120, 1965-1978.
72. M. Shimano, A. Matsuo, Tetrahedron 1998, 54, 4787-4810.
73. a) G. Cainelli, M. DaCol, P. Galletti, D. Giacomini, Synlett 1997, 923-924;
74. b) O. Kanno, M. Miyauchi, I. Kawamoto, Heterocycles 2000, 53, 173-181.
75. a) T.-A. Mitsudo, S.-W. Zhang, N. Satake, T. Kondo, Y. Watanabe, Tetrahedron Lett. 1992, 33, 5533-5536;
76. b) S.-W. Zhang, T.-A. Mitsudo, T. Kondo, Y. Watanabe, J. Organomet. Chem. 1995, 485, 55-62.
77. T. Tatsumi, K. Hashimoto, H. Tominaga, Y. Mizuta, K. Hata, H. Hidai, Y. Uchida, J. Organomet. Chem. 1983, 252, 105-112.
78. G. Delogu, G. Faedda, S. Gladiali, J. Organomet. Chem. 1984, 268, 167-174.
79. P. Barolo, P. F. Rossi, Ann. Chim. 1969, 59, 268-274.
80. T. Murai, Y. Kasai, H. Ishihara, S. Kato, J. Org. Chem. 1992, 57, 5542-5545.
81. a) A. J. Hubert, A. Georis, R. Warin, P. Teyssié, J. Chem. Soc., Perkin Trans. 2 1972, 366-370;
82. b) A. J. Hubert, P. Moniotte, G. Goebbels, R. Warin, P. Teyssié, J. Chem. Soc., Perkin Trans. 2 1973, 1954-1957.
83. B. Neugnot, J. C. Cintrat, B. Rousseau, Tetrahedron 2004, 60, 3575-3579.
84. For a review see: S. Otsuka, K. Tani, Synthesis 1991, 9, 665-680.
85. a) R. Schmid, H.-J. Hansen, Helv. Chim. Acta 1990, 73, 1258-1275;
86. b) R. Schmid, M. Cereghetti, B. Heiser, P. Schönholzer, H.-J. Hansen, Helv. Chim. Acta 1988, 71, 897-929.
87. a) K. Tani, T. Yamagata, S. Otsuka, S. Akutagawa, H. Kumobayashi, T. Taketomi, H. Takaya, A. Miyashita, R. Noyori, J. Chem. Soc., Chem. Commun. 1982, 600-601;
88. b) K. Tani, T. Yamagata, S. Akugatagawa, H. Kumobayashi, T. Taketomi, H. Takaya, A. Miyashita, R. Noyori, S. Otsuka, J. Am. Chem. Soc. 1984, 106, 5208-5217.
89. a) S.-I. Inoue, H. Takaya, K. Tani, S. Otsuka, T. Sato, R. Noyori, J. Am. Chem. Soc. 1990, 112, 4897-4905;
90. b) For ab initio study see: M. Yamakawa, R. Noyori, Organometallics 1992, 11, 3167-3169.
91. C. Chapuis, 2002, US Patent 6,350,910 B1.
92. H. Yamada, M. Sodeoka, M. Shibasaki, J. Org. Chem. 1991, 56, 4569-4574.
93. For applications in carbohydrates chemistry see: a) D. Picq, M. Cottin, D. Anker, H. Pacheco, Tetrahedron Lett. 1983, 24, 1399-1402;
94. b) D. Picq, D. Anker, C. Rousset, A. Laurent, Tetrahedron Lett. 1983, 24, 5619-5622;
95. c) D. Picq, I. Drivas, G. Carret, D. Anker, M. Abou-Assali, Tetrahedron 1985, 41, 2681-2690;
96. d) M.-B. Giudicelli, M.-A. Thomé, D. Picq, D. Anker, Carbohydr. Res. 1993, 249, 19-37;
97. e) D. Picq, G. Carret, D. Anker, Carbohydr. Res. 1986, 149, 458-463.
98. Q. Liu, A. P. Marchington, N. Boden, C. M. Rayner, J. Chem. Soc., Perkin Trans. 1 1997, 511-525.
99. a) H. A. J. Carless, D. J. Haywood, J. Chem. Soc., Chem. Commun. 1980, 980-981;
100. b) R. Boss, R. Scheffold, Angew. Chem. Int. Ed. Engl. 1976, 15, 558-559.
101. S. Jaime-Figueroa, Y. Liu, J. M. Muchowski, D. G. Putman, Tetrahedron Lett. 1998, 39, 1313-1316.
102. H. Tomori, K. Shibutami, K. Ogura, Heterocycles 1997, 44, 213-225.
103. [98]
104. M. S. Furness, X. Zhang, A. Coop, A. E. Jacobson, R. B. Rothman, C. M. Dersch, H. Xu, F. Porreca, K. C. Rice, J. Med. Chem. 2000, 43, 3193-3196.
105. M. Karpf, R. Trussardi, J. Org. Chem. 2001, 66, 2044-2051.
106. K. Afarinkia, C. W. Rees, J. I. G. Cadogan, Tetrahedron 1990, 46, 7175-7196.
107. N. K. Chauduri, O. Servando, B. Markus, I. Galynker, M.-S. Sung, J. Indian Chem. Soc. 1985, 62, 899-903.
108. S. K. Nayak, S. M. Kadam, A. Banerji, Synlett 1993, 581-582.
109. a) S. Talukdar, A. Banerji, J. Indian Chem. Soc. 1997, 74, 842-847;
110. b) S. Rele, S. Chattopadhyay, S. K. Nayak, Tetrahedron Lett. 2001, 42, 9093-9096.
111. S. Rele, S. Talukdar, A. Banerji, Tetrahedron Lett. 1999, 40, 767-770.
112. E. Alonso, D. J. Ramon, M. Yus, Tetrahedron 1997, 53, 14355-14368.
113. D. J. Ramon, M. Yus, Tetrahedron 1996, 52, 13739-13750.
114. A. Merz, T. Meyer, Synthesis 1999, 94-99.
115. E. Vilsmaier, G. Milch, U. Bergsträsser, Tetrahedron 1998, 54, 6403-6414.
116. M. P. Bertrand, S. Escoubet, S. Gastaldi, V. I. Timokhin, Chem. Commun. 2002, 216-217.
117. S. Escoubet, S. Gastaldi, V. I. Timokhin, M. P. Bertrand, D. Siri, J. Am. Chem. Soc. 2004, 126, 12343-12352.
118. A. J. Fielding, B. P. Roberts, Tetrahedron Lett. 2001, 42, 4061-4064.
119. According to DFT calculations the S-H BDE in pentafluorophenol is 17 kJ mol-1 stronger than in thiocresol; D. Siri unpublished results.
120. R. O. Schoenleber, B. Giese, Synlett 2003, 501-504.
121. S. Das, J. S. D. Kumar, K. Shivaramayya, M. V. George, Tetrahedron 1996, 52, 3425-3434.
122. J. S. Yadav, S. Chandrasekhar, G. Sumithra, R. Kache, Tetrahedron Lett. 1996, 37, 6603-6606.
123. J.-M. Hah, L. J. Roman, R. B. Silverman, Bioorg. Med. Chem. 2000, 8, 1931-1936.
124. B. A. McGaw, R. Horgan, Phytochemistry 1983, 22, 1103-1105.
125. G. A. Dzemileva, V. N. Odinov, U. M. Dzemilev, Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl. 1988, 37, 1929-1932.
126. M. Mori, Y. Ban, Chem. Pharm. Bull. 1976, 24, 1992-1999.
127. F. Garro-Helion, A. Merzouk, F. Guibé, J. Org. Chem. 1993, 58, 6109-6613.
128. For the deprotection of monoallylamines see: a) J. K. Pak, M. Hesse, J. Org. Chem. 1998, 63, 8200-8204;
129. b) J. M. Aurrecoechea, A. Fernandez, J. M. Gogojo, R. Suero, Synth. Commun. 2003, 33, 693-702;
130. c) M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 5315-5316;
131. d) D. J. Burkhart, B. Twamley, N. R. Natale, Tetrahedron Lett. 2001, 42, 8415-8418;
132. e) F.-A. Marcotte, W. D. Lubell, Org. Lett. 2002, 4, 2601-2604;
133. f) C. Koradin, N. Gommerman, K. Polborn, P. Knochel, Chem. Eur. J. 2003, 9, 2797-2811.
134. For examples of the release of primary amines from N,N-diallylamines see: a) A. E. Jensen, P. Knochel, J. Organomet. Chem. 2002, 653, 122-128;
135. b) N. Millot, C. Piazza, S. Avolio, P. Knochel, Synthesis 2000, 941-948;
136. c) C. Goulaouic-Dubois, A. Guggisberg, M. Hesse, Tetrahedron 1995, 51, 12573-12582;
137. d) M. Takamura, K. Funabashi, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 6801-6808;
138. e) E. Vilsmaier, G. Torsten, Synthesis 1988, 739-744;
139. f) A. P. A. Arboré, D. J. Cane-Honeysett, I. Coldham, M. L. Middleton, Synlett 2000, 236-238;
140. g) G. K. S. Prakash, M. Mandal, S. Schweizer, N. A. Petasis, G. O. Olah, J. Org. Chem. 2002, 67, 3718-3723;
141. h) K. Stroemgaard, M. J. Brierley, K. Andersen, F. A. Slok, I. R. Mellor, P. N. R. Usherwood, P. Krogsgaard-Larsen, J. W. Jaroszewski, J. Med. Chem. 1999, 42, 5224-5234.
142. a) S. G. Davies, D. R. Fenwick, Chem. Commun. 1997, 567-568;
143. b) A. M. Chippindale, S. G. Davies, K. Iwamoto, R. M. Parkin, C. A. P. Smethurst, A. D. Smith, H. Rodriguez-Solla, Tetrahedron 2003, 59, 3253-3265.
144. H. Tsukamoto, T. Suzuki, Y. Kondo, Synlett 2003, 1105-1108.
145. a) S. Lemaire-Audoire, M. Savignac, J.-P. Genèt, J.-M. Bernard, Tetrahedron Lett. 1995, 36, 1267-1270;
146. b) S. Lemaire-Audoire, M. Savignac, C. Dupuis, J.-P. Genêt, Bull. Soc. Chim. Fr. 1995, 132, 1157-1166;
147. c) M. K.-H. Doll, D. E. Nichols, J. D. Kilts, C. Prioleau, C. P. Lawler, M. M. Lewis, R. B. Mailman, J. Med. Chem. 1999, 42, 935-940;
148. d) E. Lorthiois, I. Marek, J. F. Normant, J. Org. Chem. 1998, 63, 566-574;
149. e) H. G. Aurich, M. Soeberdt, K. Harms, Tetrahedron 1999, 55, 1249-1270;
150. f) V. Floch, G. Le Bolc'h, C. Gable-Guillaume, N. Le Bris, J.-J. Yaouanc, H. Des Abbayes, C. Férec, J.-C. Clément, Eur. J. Med. Chem. 1998, 33, 923-934;
151. g) D. Limal, V. Semetey, P. Dalbon, M. Jolivet, J.-P. Briand, Tetrahedron Lett. 1999, 40, 2749-2752;
152. h) I. C. Baldwin, P. Briner, M. D. Eastgate, D. J. Fox, S. Warren, Org. Lett. 2002, 4, 4381-4384.
153. a) M. Honda, H. Morita, I. Nagakura, J. Org. Chem. 1997, 62, 8932-8936;
154. b) J. P. Collman, M. Zhong, S. Costanzo, C. Zhang, J. Org. Chem. 2001, 66, 8252-8256.
155. For a review see: F. Guibé, Tetrahedron 1998, 54, 2967-3042.
156. For a general review on the hydrogenolysis of allylic and propargylic compounds see: J. Tsuji, T. Mandai, Synlett 1996, 1-24.
157. T. Kock, M. Hesse, Synthesis 1992, 931-932.
158. A. Bourgeois-Cury, D. Doan, J. Gore, Tetrahedron Lett. 1992, 33, 1277-1280.
159. S. Chandrasekhar, Ch. R. Reddy, R. J. Rao, Tetrahedron 2001, 57, 3435-3438.
160. a) X. Qian, F. Moris-Varas, M. C. Fitzgerald, C.-H. Wong, Bioorg. Med. Chem. 1996, 4, 2055-2069;
161. b) For a previous example see: E. Keinan, N. Greenspoon, Tetrahedron Lett. 1982, 23, 241-244.
162. G. Giambastiani, B. Pacini, M. Porcelloni, G. Poli, J. Org. Chem. 1998, 63, 804-807.
163. a) M. Pal, K. Parasuraman, K. R. Yeleswarapu, Org. Lett. 2003, 5, 349-352;
164. b) H. Nakamura, S. Onagi, T. Kamakura, J. Org. Chem. 2005, 70, 2357-2360.
165. K. M. Nicholas, Acc. Chem. Res. 1987, 20, 207-214.
166. P. Magnus, M. Ladlow, J. Elliott, C. S. Kim, J. Chem. Soc., Chem. Commun. 1989, 518-520.
167. B. Alcaide, J. Pérez-Castells, B. Sanchez-Vigo, M. A. Sierra, J. Chem. Soc., Chem. Commun. 1994, 587-588.
168. a) H. Kapnang, G. Charles, Tetrahedron Lett. 1983, 24, 3233-3236;
169. b) B. Ruttens, J. Van der Eycken, Tetrahedron Lett. 2002, 43, 2215-2222.
170. P. Magnus, L. S. Thurston, J. Org. Chem. 1991, 56, 1166-1170.
171. G. F. Solberghe, I.E. Marko, Tetrahedron Lett. 2002, 43, 5061-5066.
172. P. I. Kitov, D. R. Bundle, Org. Lett. 2001, 3, 2835-2838.
173. P. J. Connolly, K. N. Beers, S. K. Wetter, W. V. Murray, Tetrahedron Lett. 2000, 41, 5187-5191.
174. J. Barluenga, F. J. Fananas, R. Sanz, C. Marcos, J. M. Ignacio, Chem. Commun. 2005, 933-935.
175. J. Barluenga, J. F. Fananas, R. Sanz, Y. Fernandez, Tetrahedron Lett. 1999, 40, 1049-1052.
176. J. Barluenga, R.-M. Canteli, J. Florez, J. Org. Chem. 1996, 61, 3646-3649.
177. J. A. Murphy, K. A. Scott, R. S. Sinclair, C. Gonzalez Martin, A. R. Kennedy, N. Lewis, J. Chem. Soc., Perkin Trans. 1 2000, 2395-2408.
178. H. Ito, T. Taguchi, Y. Hauzawa, J. Org. Chem. 1993, 58, 774-775.
179. T. Taniguchi, K. Ogasawara, Tetrahedron Lett. 1998, 39, 4679-4682.
180. T. Taniguchi, K. Ogasawara, Angew. Chem. Int. Ed. 1998, 37, 1136-1137.
181. D. Necas, M. Tursky, M. Kotora, J. Am. Chem. Soc. 2004, 126, 10222-10223.
182. E. Wenkert, J. B. Fernandes, E. L. Michelotti, C. S. Swindell, Synthesis 1983, 701-703.