Pd(OAc)2-catalyzed carbonylation of amines

Journal of Organic Chemistry

Volumn 71, Issue 16, 2006, Pages 5951-5958

  Orito, Kazuhiko ^a   Miyazawa, Mamoru ^a   Nakamura, Takatoshi ^a   Horibata, Akiyoshi ^a   Ushito, Harumi ^a   Nagasaki, Hideo ^a   Yuguchi, Motoki ^a   Yamashita, Satoshi ^a   Yamazaki, Tetsuro ^a   Tokuda, Masao ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBONYLATION; CATALYSIS; CHELATION; ESTERS; ORGANOMETALLICS; PALLADIUM; TOLUENE; UREA;

AROMATIC CARBONYLATION; CHELATION EFFECTS; DIALKYLAMINE; DIALKYLUREAS;

AMINES;

ALIPHATIC AMINE; ALKYL GROUP; AMINE; AROMATIC COMPOUND; BENZENE DERIVATIVE; BENZYLAMINE; CARBAMIC ACID DERIVATIVE; CARBON; CARBON MONOXIDE; CHLORIDE; ESTER DERIVATIVE; HYDROXYL GROUP; LACTAM; PALLADIUM; PHENETHYLAMINE DERIVATIVE; PHENYL GROUP; PHOSPHINE; TOLUENE; UREA DERIVATIVE;

ARTICLE; CARBONYLATION; CATALYSIS; CHELATION; CHEMICAL MODIFICATION; CHEMICAL REACTION; STEREOSPECIFICITY;

EID: 33746892686     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060612n     Document Type: Article

References (179)

1. For general reviews, see: (a) Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation, Direct Synthesis of Carbonyl Compounds; Plenum Press: New York, 1991.
2. (b) Tsuji, J. Palladium Reagents and Catalysts, Innovation in Organic Synthesis; John Wiley & Sons: Chichester, U.K., 1995.
3. Tkatchenko, I. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 8, pp 101-223.
4. Se: (a) Sonoda, N.; Yasuhara, T.; Kondo, K.; Ikeda, T.; Tsutsumi, S. J. Am. Chem. Soc. 1971, 93, 6433.
5. (b) Kondo, K.; Sonoda, N.; Tsutsumi, S. J. Chem. Soc., Chem. Commun. 1972, 307.
6. (c) Kondo, K.; Sonoda, N.; Yoshida, K.; Koishi, M.; Tsutsumi, S. Chem. Lett. 1972, 401.
7. (d) Kondo, K.; Murata, K.; Miyoshi, N.; Murai, S.; Sonoda, N. Synthesis 1979, 735.
8. (e) Yashida, T.; Kambe, N.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1986, 27, 3037
9. Bull. Chem. Soc. Jpn. 1987, 60, 1793.
10. (f) Fujiwara, S.; Miyoshi, N.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Phys. Org. Chem. 1993, 65, 699.
11. (g) A review, Sonoda, N. Pure Appl. Chem. 1993, 65, 699.
12. (h) For ionic Se, see: Kim, H. S.; Kim, Y. J.; Lee, H.; Lee, S. D.; Chin, C. S. J. Catal. 1999, 184, 526.
13. (i) Yang, Y.; Lu, S. Tetrahedron Lett. 1999, 40, 4845.
14. (j) Kim, H. S.; Kim, Y. J.; Lee, H.; Lee, S. D.; Park, K. U.; Lee, C.; Chin, C. S. Angew. Chem., Int. Ed. 2002, 41, 4300.
15. (k) Kihlberg, T.; Karhad, F.; Långström, B. J. Org. Chem. 2002, 67, 3687.
16. (l) Mei, J.; Yang, Y.; Xue, Y.; Lu, S. J. Mol. Catal. A 2003, 191, 135.
17. (m) Chen, J.; Ling, G.; Lu, S. Tetrahedron Lett. 2003, 59, 8251.
18. (n) Ling, G.; Chen, J.; Lu, S. J. Mol. Catal. A 2003, 202, 23.
19. (o) Ling, G.; Chen, J.; Lu, S. J. Chem. Res., Synop. 2003, 442.
20. (p) Chen, J.; Ling, G.; Lu, S. Eur. J. Org. Chem. 2003, 3446.
21. (q) Fujiwara, S.; Shikano, Y.; Shin-ike, N.; Kambe, N.; Sonoda, N. Org. Lett. 2002, 67, 6275.
22. Tl: Sonoda, N.; Yasuhara, T.; Kondo, K.; Ikeda, T.; Tsutsumi, S. Bull. Chem. Soc. Jpn. 1981, 54, 1460.
23. Hg: Tsuji, J.; Iwamoto, N. Japan Patent 6904096; Chem. Abstr. 1969, 71, 12792.
24. Nefedov, B. R.; Sergeeva, N. S.; Eidus, Ya. T. Izv. Akad. Nauk. SSSR, Khim. 1973, 807;
25. Chem. Abstr. 1973, 79, 31813.
26. Mn: (a) Calderazzo, F. Inorg. Chem. 1965, 4, 293.
27. (b) Dombek, D.; Angelici, R. J. J. Organomet. Chem. 1977, 134, 203.
28. (c) Srivastava, S. C.; Shrimal, A. K.; Srivastava, A. J. Organomet. Chem. 1991, 414, 65.
29. (d) Li, K.-T.; Peng, Y.-J. J. Catal. 1993, 143, 631.
30. Fe: (a) Dombeck, B. K.; Eidus, Ya. T. Izv. Akad. Nauk. SSSR, Khim. 1976, 1782;
31. Chem. Abstr. 1977, 86, 16056.
32. German Patent 1170396; Chem. Abstr. 1964, 61, 2979.
33. (b) Sampson, H. J., Jr. U.S. Patent 2589289; Chem. Abstr. 1952, 46, 11234.
34. (c) Dombek, B. D.; Angelici, R. J. J. Catal. 1977, 48, 433.
35. Co: (a) Sternberg, H. W.; Wender, I.; Friedel, R. A.; Orchin, M. J. Am. Chem. Soc. 1953, 75, 3148.
36. (b) Rosenthal, A. Can. J. Chem. 1962, 40, 1718.
37. (c) Benedini, F.; Nali, M.; Rindone, B.; Tollari, S.; Cenini, S.; Monica, G. La; Porta, F. J. Mol. Catal. 1986, 3, 155.
38. (d) Bassoli, A.; Rindone, B.; Tollari, S.; Chioccara, F. J. Mol. Catal. 1990, 60, 41.
39. Ni: (a) Aliev, Ya. Yu.; Romanova, I. B.; Freidlin, L. Kh. Uzb. Khim. Zh. 1961, 5, 54;
40. Chem. Abstr. 1962, 57, 8413.
41. (b) Aliev, Ya. Yu.; Romanova, I. B. Neftekhim., Akad. Nauk Turkin., SSR 1963, 204;
42. Chem. Abstr. 1964, 61, 6913.
43. (c) Martin, W. E.; Farona, M. F. J. Organomet. Chem. 1981, 206, 393.
44. (d) Hoberg, H.; Fañanás, F. J.; Riegel, H. J. J. Organomet. Chem. 1983, 254, 267.
45. (e) Giannoccaro, P.; Nobile, C. F.; Mastrorilli, P.; Ravasio, N. J. Organomet. Chem. 1991, 419, 251.
46. Cu: Brackman, W. Discuss. Faraday Soc. 1968, 122.
47. Ru: (a) Byerley, J. J.; Rempel, G. L.; Takebe, N. J. Chem. Soc., Chem. Commun. 1971, 1482.
48. Lassau, C.; Cheuvin, Y.; Lefevro, G. Ger. Offen. 1902560; Chem. Abstr. 1970, 72, 21358.
49. Yamahara, T.; Takamatsu, S.; Hirose, K. Japan Kokai 72 34341; Chem. Abstr. 1973, 78, 43087.
50. (b) With Rh, Pt and Ir: Fukuoka, S.; Chono, M.; Kohno, M. J. Org. Chem. 1984, 49, 1458.
51. (c) Taqui Khan, M. M.; Halligudi, S. B.; Abdi, S. H. R.; Shukla, S. J. Mol. Catal. 1988, 48, 25.
52. (d) Taqui Khan, M. M.; Halligudi, S. B.; Shukla, S.; Abdi, S. H. R. J. Mol. Catal. 1989, 51, 129.
53. (e) With Rh, Mulla, S. A. R.; Gupte, S. P.; Chaudhari, R. V. J. Mol. Catal. 1991, 67, L7.
54. (f) With Rh, Mulla, S. A. R.; Rode, C. V.; Kelkar, A. A.; Gupte, S. P. J. Mol. Catal. A 1997, 122, 103.
55. (g) Kondo, T.; Kotachi, S.; Tsuji, Y.; Watanabe, Y.; Mitsudo, T. Organometallics 1997, 16, 2562.
56. Rh: Durand, D.; Lassau, C. Tetrahedron 1969, 28, 2329.
57. Pd: (a) Tsuji, J.; Iwamoto, N. Chem. Commun. 1966, 380.
58. (b) Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327.
59. Dieck, H. A.; Laine, R. M.; Heck, R. F. J. Org. Chem. 1975, 40, 2819.
60. (c) Ozawa, F.; Soyama, H.; Yamamoto, T.; Yamamoto, A. Tetrahedron Lett. 1982, 23, 3383.
61. (d) Ozawa, F.; Sugimoto, T.; Yuasa, Y.; Santra, M.; Yamamoto, T.; Yamamoto, A. Organometallics 1984, 3, 683.
62. (e) Ozawa, F.; Sugimoto, T.; Yamamoto, T.; Yamamoto, A. Organometallics 1984, 3, 692.
63. (f) Fukuoka, S.; Chono, M.; Kohno, M. J. Chem. Soc., Chem. Commun. 1984, 399.
64. (g) Sheludyakov, Y. L.; Golodov, V. A. Bull. Chem. Soc. Jpn. 1984, 57, 251.
65. (h) Alper, H.; Hartstock, F. W. J. Chem. Soc., Chem. Commun. 1985, 1142.
66. (i) Ozawa, F.; Soyama, H.; Yanagihara, H.; Aoyama, I.; Takino, H.; Izawa, K.; Yamamoto, T.; Yamamoto, A. J. Am. Chem. Soc. 1985, 107, 3235.
67. (j) Ozawa, F.; Yanagihara, H.; Yamamoto, A. J. Org. Chem. 1986, 51, 415.
68. (k) Tam, W. J. Org. Chem. 1986, 51, 2977.
69. (l) Murahashi, S.; Mitsue, Y.; Ike, K. J. Chem. Soc., Chem. Commun. 1987, 125.
70. (m) Giannoccaro, P. J. Organomet. Chem. 1987, 336, 271.
71. (n) Alper, H.; Vasapollo, G.; Hartstock, F. W.; Mlekuz, M. Organometallics 1987, 6, 2391.
72. (o) Gupte, S. P.; Chaudhari, R. V. J. Catal. 1988, 114, 246.
73. (p) Pri-Bar, I.; Alper, H. Can. J. Chem. 1990, 68, 1544.
74. (q) Choudary, B. M.; Rao, K. K.; Pirozhkov, S. D.; Lapidus, A. L. Synth. Commun. 1991, 21, 1923.
75. (r) Kelkar, A. A.; Kolhe, D. S.; Kanagasabapathy, S. R.; Chaudhari, V. Ind. Eng. Chem. Res. 1992, 31, 172.
76. (s) Cf. Gupte, S. P.; Chaudhari, R. V. Ind. Eng. Chem. Res. 1992, 31, 2069.
77. (t) Dahlen, G. M.; Sen, A. Macromolecules 1993, 26, 1784.
78. (u) Imada, Y.; Mitsui, Y.; Ike, K.; Washizuka, K.; Murahashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 2079.
79. Pd on Zr: (a) Giannoccaro, P.; Nobile, C. F.; Moro, G.; Ginestra, A. La; Ferragina, C.; Massucci, M. A.; Patrono, P. J. Mol. Catal. 1989, 53, 349.
80. (b) Shi, F.; Deng, Y.; SiMa, T.; Yang, H. Tetrahedron Lett. 2001, 42, 2161.
81. Pd in electrolytic oxidation: (a) Yang, H.; Deng, Y.; Shi, F. J. Mol. Catal. A 2001, 176, 73.
82. (b) Chiarotto, I.; Feroci, M. Tetrahedron Lett. 2001, 42, 3451.
83. (c) Chiarotto, I.; Feroci, M. J. Org. Chem. 2003, 68, 7137.
84. 2: (a) Gabriele, B.; Salerno, G.; Brindisi, D.; Costa, M.; Chiusoli, G. P. Org. Lett. 2000, 2, 625.
85. (b) Gabriele, B.; Mancuso, R.; Salerno, G.; Costa, M. J. Org. Chem. 2003, 68, 601.
86. (c) Gabriele, B.; Mancuso, R.; Salerno, G.; Costa, M. Chem. Commun. 2003, 406.
87. (d) Gabriele, B.; Salerno, G.; Mancuso, R.; Costa, M. J. Org. Chem. 2004, 69, 4741.
88. W: (a) Patterson, J. A.; Atwell, H. V. U.S. Patent 2993931; Chem. Abstr. 1962, 56, 1392.
89. (b) German Patent 1158494; Chem. Abstr. 1964, 61, 11900.
90. (c) German Patent 1163311; Chem. Abstr. 1964, 60, 15744.
91. (d) McCusker, J. E.; Grasso, C. A.; Main, A. D.; McElwee-White, L. Org. Lett. 1999. 1, 961
92. (e) McCusker, J. E.; Qian, F.; McElwee-White, L. J. Mol. Catal. A 2000, 159, 11.
93. (f) McCusker, J. E.; Main, A. D.; Johnson, K. S.; Grasso, C. A.; McElwee-White, L. J. Org. Chem. 2000, 65, 5216.
94. (g) Qian, F.; McCusker, J. E.; Zhang, Y.; Main, A. D.; Chlebowski, M.; Kokka, M.; McElwee-White, L. J. Org. Chem. 2002, 67, 4086.
95. (h) Hylton, K.-G.; Main, A. D.; McElwee-White, L. J. Org. Chem. 2003, 68, 1615.
96. Pt: (a) Kucheryavyi, I.; Gorlovskii, D. M.; Al'tshuler, L. N.; Zinov'ev, G. N.; Karlik, A. B.; Klopina, N. A. USR 371210; Chem. Abstr. 1973, 79, 18161.
97. Au: Shi, F.; Y. Deng, Y. J. Catal. 2002, 211, 548.
98. For classical methods for preparation of ureic derivatives using phosgene and other carbonylation reagents and their biological activities, see Gabriele's well-reviewed paper, ref 16d and references therein.
99. A little more air (oxygen) is slowly supplied through the surface of the balloon during the reaction (Knudsen flow; for a review, see: Steckelmacher, W. Rep. Prog. Phys. 1986, 49, 1083).
100. (a) Fuchita, Y. Tsuchiya, H. Polyhedron 1993, 12, 2079;
101. Inorg. Chim. Acta 1993, 209, 229.
102. (b) Vicente, J.; Saura-Llamas, I.; Palin, M. J.; Jones, P. G.; Ramírez de Arellano, M. C. Organometallics 1997, 16, 826.
103. Onto, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Tokuda, M. Presented at the 31th Congress of Heterocyclic Chemistry, Kitakyushu, Japan, October 2000; Abstract, p 147.
104. 2.
105. Hosokawa, T.; Murahashi, S. Acc. Chem. Res. 1990, 23, 49.
106. Onto, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, M.; Tokuda, M. J. Am. Chem. Soc. 2004, 126, 14342.
107. 8, see: (a) Murahash, S.; Horiie, S. J. Am. Chem. Soc. 1955, 77, 6403.
108. (b) Murahashi, S.; Horiie, S. J. Am. Chem. Soc. 1956, 78, 4816.
109. (c) Rosenthal, A.; Astbury, R. F.; Hubscher, A. J. Am. Chem. Soc. 1958, 23, 1037.
110. (d) Rosenthal, A. Can. J. Chem. 1960, 38, 2025.
111. (e) Rosenthal, A.; Hubscher, H. J. Org. Chem. 1969, 25, 1562.
112. (f) Rosenthal, A.; Weir, M. R. S. Can. J. Chem. 1962, 40, 610;
113. J. Org. Chem. 1963, 28, 3025.
114. (g) Rosenthal, A.; Millward, S. Can. J. Chem. 1963, 41, 2504;
115. Can. J. Chem. 1964, 42, 956.
116. (h) Rosenthal, A.; Gervay, J. Can. J. Chem. 1964, 42, 1490.
117. (i) Rosenthal, A.; Yalpani, M. Can. J. Chem. 1965, 43, 711, 3449.
118. (j) Murahashi, S.; Horiie, T.; Jo, T. Bull. Chem. Soc. Jpn. 1960, 33, 81.
119. (k) Horiie, S.; Murahashi, S. Bull. Chem. Soc. Jpn. 1960, 33, 88.
120. (l) Horiie, S.; Murahashi, S. Bull. Chem. Soc. Jpn. 1960, 33, 247.
121. (m) Kajimoto, T.; Tsuji, J. J. Org. Chem. 1983, 48, 1685.
122. 6, see: (n) Mori, Y.; Tsuji, J. Tetrahedron 1971, 27, 3811.
123. For recent reviews on carbonylation of cyclopalladation products, see: (a) Ryabov, A. D. Synthesis 1985, 233.
124. (b) Reference 1b, pp 87-94.
125. For carbonylation of cyclopalladation products, leading to the formation of benzolactams, see: (a) Takahashi, H.; Tsuji, J. J. Organomet. Chem. 1967, 10, 511.
126. (b) Thompson, J. M.; Heck, R. F. J. Org. Chem. 1975, 40, 2667.
127. (c) Yamamoto, Y.; Yamazaki, H. Synthesis 1976, 750.
128. For esters, see: (d) Izumi, T.; Katou, T.; Kusahara, A.; Hanaya, K. Bull. Chem. Soc. Jpn. 1978, 51, 3407.
129. (e) Kasahara, A.; Izumi, T.; Maemura, M. Bull. Chem. Soc. Jpn. 1977, 50, 1878.
130. (f) Kamiyama, S. I.; Kamura, T. Kasahara, A.; Izumi, T.; Maemura, M. Bull. Chem. Soc. Jpn. 1979, 52, 142.
131. (g) Kasahara, A.; Izumi, T.; Watanabe, H. Bull. Chem. Soc. Jpn. 1979, 52, 957.
132. (h) Sokolov, V. I.; Troitskaya, L. L.; Reutov, O. A. J. Organomet. Chem. 1979, 182, 537.
133. (i) Nielson, A. J. J. Chem. Soc., Dalton Trans. 1981, 205.
134. (j) Izumi, T.; Maemura, M.; Endoh, K.; Oikawa, T.; Zakozi, S.; Kasahara, A. Bull. Chem. Soc. Jpn. 1981, 54, 836.
135. (k) Horino, H.; Inoue, N. J. Org. Chem. 1981, 46, 4416.
136. (l) Troitskaya, L. L.; Khruschova, N. S.; Sokolov, V. I.; Reutov, O. A. Zh. Org. Khim. 1982, 18, 2606;
137. Chem. Abstr. 1983, 98, 126327.
138. (m) Sokolov, V. I. Pure Appl. Chem. 1984, 55, 1837.
139. Other examples of direct aromatic carbonylations. For Pd(II)-catalyzed carbonylation of benzene to benzoic acid, see: (a) Fujiwara, Y.; Kawauchi, T.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1980, 220.
140. (b) Jintoku, T.; Taniguchi, H.; Fujiwara, Y. Chem. Lett. 1987, 1159.
141. (c) Jintoku, T.; Fujiwara, Y.; Kawata, I.; Kawauchi, T.; Taniguchi, H. J. Organomet. Chem. 1990, 385, 297.
142. (d) Taniguchi, Y.; Yamaoka, Y.; Nakata, K.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1995, 345.
143. (e) Lu, W.; Yamaoka, Y.; Taniguchi, Y.; Kitamura, T.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1999, 580, 290.
144. For reviews, see: (f) Fujiwara, Y.; Takaki, K. Taniguchi, Y. Synlett 1996, 591.
145. (g) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
146. 2, see: (a) Fisher, B. J.; Eisenberg, R. K. Organometallics 1983, 2, 764.
147. (b) Kunin, A. J.; Eisenberg, R. K. J. Am. Chem. Soc. 1986, 108, 535.
148. (c) Kunin, A. J.; Eisenberg, R. K. Organometallics 1988, 7, 2124.
149. 2, see: (d) Sakakura, T.; Tanaka, M. Chem. Lett. 1987, 249.
150. (e) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221.
151. (f) Boyd, S. E.; Field, L. D.; Partridge, M. G. J. Am. Chem. Soc. 1994, 116, 9492.
152. (g) Rosini, G. P.; Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1994, 116, 9498.
153. 3), see: (h) Gordon, E. M.; Eisenberg, R. J. Mol. Catal. 1988, 45, 57.
154. 12, see: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888.
155. (b) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1966, 118, 493.
156. (c) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604.
157. (d) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647.
158. (e) Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129.
159. (f) Fukuyama, T.; Chatani, N.; Tatsumi, J.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1998, 120, 11522.
160. (g) Ie, Y.; Chatani, N.; Ogo, T.; Marshall, D. R.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 1475.
161. (h) Chatani, N.; Fukuyama, T.; Tatamidani, H.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2000, 65, 4039.
162. (i) Chatani, N.; Yorimitsu, S.; Asaumi, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2002, 67, 7557.
163. (j) Asaumi, T.; Chatani, N.; Matsuo, T.; Kakiuchi, F.; Murai, S. J. Org. Chem. 2003, 68, 7538.
164. 12, see: (k) Asaumi, T.; Matsuo, T.; Fukuyama, T.; Ie, Y.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 4433.
165. (l) Hong, P.; Yamazaki, H. Chem. Lett. 1979, 1335.
166. 2, see: (m) Takeuchi, R.; Yasue, H. J. Org. Chem. 1993, 58, 5386.
167. (n) Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6941.
168. For other examples of direct aromatic carbonylations via O-aryl palladium species, see: (a) Koyasu, Y.; Matsuzaka, H.; Hiroe, Y.; Uchida, Y.; Hidai, M. J. Chem. Soc., Chem. Commun. 1987, 575.
169. (b) Matsuzaka, H.; Hiroe, Y.; Iwasaki, M.; Ishii, Y.; Koyasu, Y.; Hidai, M. Chem. Lett. 1988, 377.
170. (c) Matsuzaka, H.; Hiroe, Y.; Iwasaki, M.; Ishii, Y.; Koyasu, Y.; Hidai, M. J. Org. Chem. 1988, 55, 3832.
171. (d) Iwasaki, M.; Matsuzaka, H.; Hiroi, Y.; Ishii, Y.; Koyasu, Y.; Hidai, M. Chem. Lett. 1988, 1159.
172. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
173. (f) Ishii, Y.; Hidai, M. J. Organomet. Chem. 1992, 428, 279.
174. (a) Mori, M.; Chiba, K.; Ban, Y. J. Org. Chem. 1978, 43, 1684.
175. (b) Mori, M.; Chiba, K.; Inotsume, N.; Ban, M. Heterocycles 1979, 12, 921.
176. 12; see: (a) Liang, C. D. Tetrahedron Lett. 1986, 27, 1971.
177. (b) Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1997, 70, 3117 and references therein.
178. (c) Reference 32g.
179. Orito, K.; Hatakeyama, T.; Takeo, M.; Uchiito, S.; Tokuda, M.; Suginome, H. Tetrahedron 1998, 54, 8403.