Scandium triflate in organic synthesis

European Journal of Organic Chemistry

Volumn , Issue 1, 1999, Pages 15-27

  Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Catalyst; Lewis acid; Organic synthesis; Stereoselective reaction

Indexed keywords

HYDRAZONE DERIVATIVE; IMINE; LANTHANIDE; MESYLIC ACID; SCANDIUM; YTTRIUM;

CATALYSIS; CATALYST; CHEMICAL REACTION; REVIEW; STEREOCHEMISTRY; SYNTHESIS; WATER ANALYSIS;

EID: 0032770704     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199901)1999:1<15::AID-EJOC15>3.0.CO;2-B     Document Type: Review

References (170)

1. F. A. Cotton, G. Wilkinson, Advanced Inorganic Chemistry, 5th ed., Wiley, New York, 1988, p. 973.
2. S. Kobayashi, I. Hachiya, M. Araki, H. Ishitani, Tetrahedron Lett. 1993, 34, 3755-3758.
3. [3a] S. Kobayashi, Chem. Lett. 1991, 2187-2190.
4. [3b] S. Kobayashi, Synlett 1994, 689-701 and references cited therein. -
5. See also: [3c] R. W. Marshman, Aldrichim. Acta 1995, 28, 77-84.
6. S. Kobayashi, I. Hachiya, H. Ishitani, M. Araki, Synlett 1993, 472-474.
7. Other examples: Addition reaction of lithium enolates of ketones to 1,2-epoxides to afford a-alkyl-γ-hydroxy ketones: [5a] P. Crotti, V. D. Bussolo, L. Favero, M. Pineschi, M. Pasero, J. Org. Chem. 1996, 61, 9548-9552. -
8. The cross-aldol reactions between ketones and aldehydes: [5b] S. Fukuzawa, T. Tsuchimoto, T. Kanai, Bull. Chem. Soc. Jpn. 1994, 67, 2227-2232.
9. [6a] C. J. Li, Chem. Rev. 1993, 93, 2023-2035.
10. [6b] A. Lubineau, J. Ange, Y. Queneau, Synthesis 1994, 741-760.
11. S. Kobayashi, T. Wakabayashi, S. Nagayama, H. Oyamada, Tetrahedron Lett. 1997, 38, 4559-4562.
12. Judging from the amount of the surfactant used in the present case, the aldol reaction would not proceed only in micelles: [8a] J. H. Fendler, E. J. Fendler, Catalysis in Micellar and Macromolecular Systems, Academic, London, 1975.
13. [8b] Mixed Surfactant Systems (Eds.: P. M. Holland, D. N. Rubingh), ACS, Washington, DC, 1992.
14. [8c] Structure and Reactivity in Aqueous Solution (Eds.: C. J. Cramer, D. G. Truhlar), ACS, Washington, DC, 1994.
15. [8d] Surfactant-Enhanced Subsurface Remediation (Eds.: D. A. Sabatini, R. C. Knox, J. H. Harwell), ACS, Washington, DC, 1994.
16. Reviews: [9a] J. K. Rasmussen, Synthesis 1977, 91-110.
17. [9b] I. Fleming, Chimia 1980, 34, 265-271.
18. [9c] P. Brownbridge, Synthesis 1983, 1-28; 85-104.
19. [9d] W. P. Weber, Silicon Reagents for Organic Synthesis, Springer-Verlag, Berlin, 1983.
20. [9e] E. W. Colvin, Chem. Soc. Rev. 1978, 7, 15-64.
21. Reviews: [10a] E. M. Gordon, R. W. Barrett, W. J. Dower, S. P. A. Fodor, M. A. Gallop, J. Med. Chem. 1994, 37, 1385-1401.
22. [10b] N. K. Terret, M. Gardner, D. W. Gordon, R. J. Kobylecki, J. Steele, Tetrahedron 1995, 51, 8135-8173.
23. [10c] G. Lowe, Chem. Soc. Rev. 1995, 37, 309-317.
24. [10d] J. S. Früchtel, G. Jung, Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42.
25. [10e] L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-600.
26. [10f] F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337.
27. S. Kobayashi, I. Hachiya, S. Suzuki, M. Moriwaki, Tetrahedron Lett. 1996, 37, 2809-2812.
28. S. Kobayashi, I. Hachiya, M. Yasuda, Tetrahedron Lett. 1996, 37, 5569-5572.
29. Review: Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.
30. For the reactions of carbonyl compounds with tetraallyltin: [14a] W. G. Peet, W. Tam, J. Chem. Soc., Chem. Commun. 1983, 853-854.
31. [14b] G. Daude, M. Pereyre, J. Organom. Chem. 1980, 190, 43-52.
32. [14c] D. N. Harpp, M. Gingras, J. Am. Chem. Soc. 1988, 110, 7737-7745.
33. [14d] S. Fukuzawa, K. Sato, T. Fujinami, S. Sakai, J. Chem. Soc., Chem. Commun. 1990, 939-940.
34. [14e] A. Yanagisawa, H. Inoue, M. Morodome, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10356-10357.
35. 3-promoted allylation reactions of carbonyl compounds were reported: [15a] Tetraallylgermanium: T. Akiyama, J. Iwai, Tetrahedron Lett. 1997, 38, 853-856.
36. [15b] Allyltrimethylsilane: V. K. Aggarwal, G. P. Vennall, Tetrahedron Lett. 1996, 37, 3745-3746. -
37. 3 is also an effective catalyst for the allylation of imines with allyltributyltin: [15c] C. Bellucci, P. G. Cozzi, A. Umani-Ronchi, Tetrahedron Lett. 1995, 36, 7289-7292.
38. [15d] S. Kobayashi, S. Nagaxama, Synlett 1997, 653-654.
39. I. Hachiya, S. Kobayashi, J. Org. Chem. 1993, 58, 6958-6960.
40. [17a] W. Schmid, G. M. Whitesides, J. Am. Chem. Soc. 1991, 113, 6674-6675.
41. [17b] E. Kim, D. M. Gordon, W. Schmid, G. M. Whitesides, J. Org. Chem. 1993, 58, 5500-5507.
42. [18a] S. Kobayashi, T. Wakabayashi, H. Oyamada, Chem. Lett. 1997, 831-832.
43. [18b] S. Kobayashi, T. Busujima, S. Nagayama, J. Chem. Soc., Chem. Commun. 1998, 981-982.
44. [19a] G. A. Olah Friedel-Crafts Chemistry, Wiley-Interscience, New York, 1973.
45. [19b] H. Heaney, Comprehensive Organic Synthesis, vol. 2 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, p. 733-752.
46. [19c] G. A. Olah, R. Krishnamurti, G. K. S. Prakash, Comprehensive Organic Synthesis, vol. 3 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, p. 293-339.
47. A. Kawada, S. Mitamura, S. Kobayashi, Synlett 1994, 545-546.
48. A. Kawada, S. Mitamura, S. Kobayashi, J. Chem. Soc., Chem. Commun. 1996, 183-184.
49. [22a] S. Kobayashi, M. Moriwaki, I. Hachiya, J. Chem. Soc., Chem. Commun. 1995, 1527-1528.
50. [22b] S. Kobayashi, M. Moriwaki, I. Hachiya, Synlett 1995, 1153-1154.
51. [22c] S. Kobayashi, M. Moriwaki, I. Hachiya, Bull. Chem. Soc. Jpn. 1997, 70, 267-273.
52. [23a] D. Yates, P. Eaton, J. Am. Chem. Soc. 1960, 82, 4436-4437.
53. [23b] T. K. Hollis, N. P. Robinson, B. Bosnich, J. Am. Chem. Soc. 1992, 114, 5464-5466.
54. -Reviews: [23c] W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990.
55. [24a] S. Kobayashi, I. Hachiya, T. Takahori, M. Araki, H. Ishitani, Tetrahedron Lett. 1992, 33, 6815-6818.
56. [24b] S. Arseniyadis, R. Rodriguez, D. V. Yashunsky, J. Camara, G. Ourisson, Tetrahedron Lett. 1994, 35, 4843-4846.
57. [24c] K. Ishihara, M. Kubota, H. Kurihara, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 4413-4414.
58. [24d] T. Sammakia, M. A. Berliner, J. Org. Chem. 1995, 60, 6652-6653.
59. Some Diels - Alder reactions in water without a catalyst were reported. For example: [25a] D. C. Rideout, R. Breslow, J. Am. Chem. Soc. 1980, 102, 7816-7817.
60. [25b] P. A. Grieco, P. Garner, Z. He, Tetrahedron Lett. 1983, 24, 1897-1900.
61. [26a] S. M. Weinreb, Comprehensive Organic Synthesis, vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 401-449.
62. [26b] D. L. Boger, S. M. Weinreb, Organic Chemistry, Hetero Diels - Alder Methodology in Organic Synthesis, vol. 47, Academic, San Diego, 1987, ch. 2 and 9.
63. S. Danishefsky, T. Kitahara, J. Am. Chem. Soc. 1974, 96, 7807-7808.
64. [28a] S. Kobayashi, H. Ishitani, S. Nagayama, Chem. Lett. 1995, 423-424.
65. [28b] S. Kobayashi, H. Ishitani, S. Nagayama, Synthesis 1995, 1195-1202.
66. [29a] V. Lucchini, M. Prato, G. Scorrano, P. Tecilla, J. Org. Chem. 1988, 53, 2251 -2258.
67. [29b] D. L. Boger, Tetrahedron 1983, 39, 2869-2939.
68. [29c] P. A. Grieco, A. Bahsas, Tetrahedron Lett. 1988, 29, 5855-5858 and references cited therein.
69. For the reactions of vinyl ethers, see: [30a] T. Joh, N. Hagihara, Tetrahedron Lett. 1967, 4199-4200.
70. [30b] L. S. Povarov, Russian Chem. Rev. 1967, 36, 656; Usp. Khim. 1967, 36, 1533-1562; Chem Abstr. 1968, 68, 2363y.
71. [30b] L. S. Povarov, Russian Chem. Rev. 1967, 36, 656; Usp. Khim. 1967, 36, 1533-1562; Chem Abstr. 1968, 68, 2363y.
72. [30b] L. S. Povarov, Russian Chem. Rev. 1967, 36, 656; Usp. Khim. 1967, 36, 1533-1562; Chem Abstr. 1968, 68, 2363y.
73. [30c] D. F. Worth, S. C. Perricine, E. F. Elslager, J. Heterocycl. Chem. 1970, 7, 1353-1356.
74. [30d] T. Kametani, H. Takeda, Y. Suzuki, H. Kasai, T. Honda, Heterocycles 1986, 24, 3385-3395.
75. [30e] Y. S. Cheng, E. Ho, P. S. Mariano, H. L. Ammon, J. Org. Chem. 1985, 50, 5678-5686, and references cited therein. -
76. For reactions of vinyl sulfides, see: [30f] K. Narasaka, T. Shibata, Heterocycles 1993, 35, 1039-1053.
77. Fujiwara et al. reported a similar type of reaction: Y. Makioka, T. Shindo, Y. Taniguchi, K. Takai, Y. Fujiwara, Synthesis 1995, 801-804.
78. J. Sisko, S. M. Weinreb, Tetrahedron Lett. 1989, 30, 3037-3040.
79. Y. Nomura, M. Kimura, Y. Takeuchi, S. Tomoda, Chem. Lett. 1978, 267-270.
80. [34a] R. Huisgen, R. Grashy, H. Hauck, H. Seidl, Chem. Ber. 1968, 101, 2043-2055.
81. [34b] J. J. Tufariello, 1,3-Dipolar Cyclo-addition Chemstry (Ed.: A. Padwa), Wiley, Chichester, 1984, vol. 2, p. 83-68.
82. [34c] K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, VCH, Weinheim, 1988.
83. [35a] S. Kanemasa, T. Uemura, E. Wada, Tetrahedron Lett. 1992, 33, 7889-7892.
84. [35b] S. Kanemasa, M. Nishiuchi, A. Kamimura, K. Hori, J. Am. Chem. Soc. 1994, 116, 2324-2339.
85. [35c] S. Murahashi, Y. Imada, M. Kohno, T. Kawakami, Synlett 1993, 395-396.
86. [35d] O. Tamura, T. Yamaguchi, K. Noe, M. Sakamoto, Tetrahedron Lett. 1993, 34, 4009-4010.
87. [35e] Y. Tokunaga, M. Ihara, K. Fukumoto, Tetrahedron Lett. 1996, 37, 6157-6160.
88. [35f] M. Shimizu, Y. Ukaji, K. Inomata, Chem. Lett. 1996, 455-456.
89. [35g] A. I. Sanchez-Blanco, K. V. Gothelf, K. A. Jorgensen, Tetrahedron. Lett. 1997, 38, 7923-7926.
90. S. Kobayashi, R. Akiyama, M. Kawamura, H. Ishitani, Chem. Lett. 1997, 1039-1040.
91. [37a] The Chemistry of the Amidines and Imidates (Ed.: S. Patai), Wiley, New York, 1975.
92. [37b] R. Roger, D. G. Neilson, Chem. Rev. 1961, 61, 179-211.
93. H. Ishitani, S. Nagayama, S. Kobayashi, J. Org. Chem. 1996, 61, 1902-1903.
94. E. F. Kleinman, Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991. vol. 2, p. 893-951.
95. [40a] S. Danishiefsky, T. Kitahara, R. McKee, P. F. Schuda, J. Am. Chem. Soc. 1976, 98, 6715-6717.
96. [40b] M. Wada, Y. Nishihara, K. Akiba, Tetrahedron Lett. 1984, 25, 5405-5408.
97. [40c] S. Danishefsky, M. Prisbylla, B. Lipisko, Tetrahedron Lett. 1980, 21, 805-808.
98. [41a] I. Ojima, S. Inaba, K. Yoshida, Tetrahedron Lett. 1977, 3643-3646.
99. [41b] G. Guanti, E. Narisano, E. Banfi, Tetrahedron Lett. 1987, 28, 4331-4334.
100. [41c] T. Mukaiyama, K. Kashiwagi, S. Matsui, Chem. Lett. 1989, 1397-1400.
101. [41d] T. Mukaiyama, H. Akamatsu, J. S. Han, Chem. Lett. 1990, 889-892.
102. [41e] M. Onaka, R. Ohno, N. Yanagiya, Y. Izumi, Synlett 1993, 141-142.
103. [41f] K. Ishihara, N. Hanaki, M. Funahashi, M. Miyata, H. Yamamoto, Bull. Chem. Soc. Jpn. 1995, 68, 1721-1730.
104. [41g] S. Kobayashi, M. Araki, M. Yasuda, Tetrahedron Lett. 1995, 36, 5773-5776.
105. [42a] K. Ikeda, K. Achiwa, M. Sekiya, Tetrahedron Lett. 1983, 24, 4707. -
106. For a stoichiometric use: [42b] J. E. Dubois, G. Axiotis, Tetrahedron Lett. 1984, 25, 2143-2146.
107. [42c] E. W. Colvin, D. G. McGarry, J. Chem. Soc., Chem. Commun. 1985, 539-540.
108. [42d] S. Shimada, K. Saigo, M. Abe, A. Sudo, M. Hasegawa, Chem. Lett. 1992, 1445-1448.
109. [42e] K. Hattori, H. Yamamoto, Tetrahedron 1994, 50, 2785-2792.
110. S. Kobayashi, M. Araki, H. Ishitani, S. Naaayama, I. Hachiya, Synlett 1995, 233-234.
111. S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu, A. R. Katritzky, Tetrahedron Lett. 1996, 37, 3731-3734.
112. S. Kobayashi, R. Akiyama, M. Moriwaki, Tetrahedron Lett. 1997, 38, 4819-4822.
113. S. Kobayashi, H. Ishitani, J. Chem. Soc., Chem. Commun. 1995, 1379.
114. S. Kobayashi, M. Moriwaki, R. Akiyama, S. Suzuki, I. Hachiya, Tetrahedron Lett. 1996, 37, 7783-7786.
115. H. Oyamada, S. Kobayashi, Synlett 1998, 249-250.
116. A. Alexakis, N. Lensen, P. Mangeney, Synlett 1991, 625-626.
117. [50a] S. Hasimoto, N. Komeshima, K. Koga, J. Chem. Soc., Chem. Commun. 1979, 437-438.
118. [50b] K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima, J. Sugimori, J. Am. Chem. Soc. 1989, 111, 5340-5345.
119. [50c] C. Chapuis, J. Jurczak, Helv. Chim. Acta 1987, 70, 436-440.
120. [50d] K. Maruoka, T. Itoh, T. Shirasaka, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310-312.
121. [50e] E. J. Corey, R. Imwinkelried, S. Pikul, Y. B. Xiang, J. Am. Chem. Soc. 1989, 111, 5493-5495.
122. [50f] D. Kaufmann, R. Boese, Angew. Chem. Int. Ed. Engl. 1990, 29, 545-546.
123. [50g] E. J. Corey, N. Imai, H. Y. Zhang, J. Am. Chem. Soc. 1991, 113, 728-729.
124. [50h] D. Sartor, J. Saffrich, G. Helmchen, C. J. Richards, H. Lambert, Tetrahedron: Asymmetry 1991, 2, 639-642.
125. [50i] K. Mikami, M. Terada, Y. Motoyama, T. Nakai, Tetrahedron: Asymmmetry 1991, 2, 643-646.
126. [50j] D. A. Evans, S. J. Miller, T. Lectka, J. Am. Chem. Soc. 1993, 115, 6460-6461.
127. [50k] K. Ishihara, Q. Gao, H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 10412-10413.
128. [50l] K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 55, 2938-2939.
129. [50m] J. P. Seerden, H. W. Scheeren, Tetrahedron Lett. 1993, 34, 2669-2672. -
130. Review: [50n] K. Narasaka, Synthesis 1991, 1-14.
131. [50o] H. B. Kagan, O. Riant, Chem. Rev. 1992, 92, 1007-1019.
132. [51a] M. Bednarski, C. Maring, S. Danishefsky, Tetrahedron Lett. 1983, 24, 3451-3454.
133. [50b] M. Quimpere, K. Jankowski, J. Chem. Soc., Chem. Commun. 1987, 676-677.
134. [51c] H. Sasai, T. Suzuki, N. Itoh, K. Tanaka, T. Date, K. Okamura, M. Shibasaki, J. Am. Chem. Soc. 1993, 115, 10372-10373, and references cited therein.
135. S. Kobayashi, I. Hachiya, H. Ishitani, M. Araki, Tetrahedron Lett. 1993, 34, 4535-4538.
136. [53a] S. Kobayashi, H. Ishitani, J. Am. Chem. Soc. 1994, 116, 4083-4084.
137. [53b] S. Kobayashi, H. Ishitani, I. Hachiya, M. Araki, Tetrahedron 1994, 50, 11623-11636.
138. S. Kobayashi, M. Araki, I. Hachiya, J. Org. Chem. 1994, 59, 3758-3759.
139. Review: F. A. Hart, Comprehensive Coordination Chemistry (Ed.: G. Wilkinson), vol. 3, Pergamon, Yew York, 1987, p. 1059.
140. S. Kobayashi, H. Ishitani, M. Araki, I. Hachiya, Tetrahedron Lett. 1994, 35, 6325-6328.
141. [57a] K. Maruoka, H. Yamamoto, J. Am. Chem. Soc. 1989, 111, 789-790.
142. [57b] J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814-3815.
143. K. Hattori, H. Yamamoto, J. Org. Chem. 1992, 57, 3264-3265.
144. [59a] M. T. Reetz, S. H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824-825.
145. [59b] K. Mikami, M. Terada, T. Nakai, J. Am. Chem. Soc. 1990, 112, 3949-3954.
146. [60a] K. Ishihara, M. Miyata, K. Hattori, T. Tada, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 10520-10524.
147. [60b] H. Waldmann, Synthesis 1994, 535-551.
148. [60c] E. Borrione, M. Prato, G. Scorrano, M. Stivanello, J. Chem. Soc., Perkin Trans. 1 1989, 2245-2250.
149. H. Ishitani, S. Kobayashi, Tetrahedron Lett. 1996, 37, 7357-7360.
150. S. Kobayashi, M. Kawamura, J. Am. Chem. Soc., 1998, 120, 5840-5841.
151. [63a] K. Ishihara, Y. Karumi, M. Kubota, H. Yamamoto, Synlett 1996, 839-841.
152. [63b] S. Fukuzawa, T. Tsucihmoto, T. Hotaka, T. Hiyama, Synlett 1995, 1077-1078.
153. [693c] V. K. Aggarwal, S. Fonquerna, G. P. Vennall, Synlett 1998, 849.
154. K. Fukase, I. Kinoshita, T. Kanoh, Y. Nakai, A. Hasuoka, S. Kusumoto, Tetrahedron 1996, 52, 3897-3904.
155. [65a] K. Ishihara, M. Kubota, H. Kurihara, H. Yamamoto, J. Org. Chem. 1996, 61, 4560-4567.
156. [65b] A. G. M. Barrett, D. C. Braddock. J. Chem. Soc., Chem. Commun. 1997, 351-352.
157. N. Yamamoto, M. Isobe, Chem. Lett. 1994, 2299-2302.
158. [67a] M. P. J. Ji, Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192.
159. [67b] M. P. Sibi, C. P. Jasperse, J. Ji, J. Am Chem. Soc. 1995, 117, 10779-10780.
160. [68a] M. Prein, A. Padwa, Tetrahedron Lett. 1996, 37, 6981-6984.
161. [68b] H. G. Bazin, R. J. Kerns, R. J. Linhardt, Tetrahedron Lett. 1997, 38, 923-926.
162. [68c] M. Prein, P. J. Manley, A. Padwa, Tetrahedron 1997, 53, 7777-7794.
163. C. B. Castellani, O. Carugo, M. Giusti, C. Leopizzi, A. Perotti, A. G. Invernizzi, G. Vidari, Tetrahedron 1996, 52, 11045-11052.
164. S. Fukuzawa, Y. Yamaishi, H. Furuya, K. Terao, F. Iwasaki, Tetrahedron Lett. 1997, 38, 7203-7206.
165. F. J. Waller, A. G. M. Barrett, D. C. Braddock, D. Ramprasad, J. Chem. Soc., Chem. Commun. 1997, 613-614.
166. [72a] M. Matsui, N. Karibe, K. Hayashi, H. Yamamoto, Bull. Chem. Soc. Jpn. 1995, 68, 3569-3571.
167. [72b] M. Matsui, H. Yamamoto, Bull. Chem. Soc. Jpn. 1995, 68, 2663-2668.
168. [73a] T. Tsuchimoto, K. Tobita, T. Hiyama, S. Fukuzawa, J. Org. Chem. 1997, 62, 6997-7005.
169. [73b] M. T. E. Gihani, H. Heaney, K. F. Shuhaibar, Synlett 1996, 871-872.
170. V. K. Aggarwal, G. P. Vennall, P. N. Davey, C. Newman, Tetrahedron Lett. 1998, 39, 1997.