Enantioselective Addition of Organozinc Reagents to Aldehydes

Chemical Reviews

Volumn 92, Issue 5, 1992, Pages 833-856

  Soai, Kenso ^a   Niwa, Seiji ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 4244117250     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr00013a004     Document Type: Article

References (201)

1. Review: Solladie, G. In Asymmetric Synthesis; Morrison, J.D., Ed., Academic Press: New York, 1983; Vol. 2A, Chapter 6.
2. Mukaiyama, T., Soai, K., Kobayashi, S. Chem. Lett. 1978, 219.
3. Soai, K., Mukaiyama, T. Chem. Lett. 1978, 491.
4. Sato, T., Soai, K., Suzuki, K., Mukaiyama, T. Chem. Lett. 1978, 601.
5. Mukaiyama, T., Soai, K., Sato, T., Shimizu, H., Suzuki, K. J. Am. Chem. Soc. 1979, 101, 1455.
6. Mazaleyrat, J.-P., Cram, D.J. J. Am. Chem. Soc. 1981, 103, 4585.
7. Eleveld, M.B., Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187.
8. Seebach, D., Beck, A.K., Roggo, S., Wonnacott, A. Chem. Ber. 1985, 118, 3673.
9. Reetz, M.T., Kukenhohner, T., Weinig, P. Tetrahedron Lett. 1986, 27, 5711.
10. Tomioka, K., Nakajima, M., Koga, K. Chem. Lett. 1987, 65.
11. Noyori, R., Suga, S., Kawai, K., Okada, S., Kitamura, M. Pure Appl. Chem. 1988, 60, 1597.
12. Soai, K., Mukaiyama, T. Bull. Chem. Soc. Jpn. 1979, 52, 3371.
13. Frankland, E. Justus Liebigs Ann. Chem. 1849, 71, 171.
14. Nutzel, K. In Methoden der Organischen Chemie; Muller, E., Ed., Georg Thieme Verlag: Stuttgart, 1973; Vol. 13, p 2a.
15. Carruthers, W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed., Pergamon Press: Oxford, 1982; Chapter 49.
16. Marx, B., Henry-Basch, E., Freon, P., C.R. Acad. Sci., Ser. C, 1967, 264, 1967.
17. EVana, D.A. Science 1988, 240, 420.
18. Soai., K. Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.) 1989, 47, 11.
19. Biystone., S.L. Chem. Rev. 1989, 89, 1663.
20. Tomioka., K. Synthesis 1990, 541.
21. Tanaka., A. Nippon NogeikagakuKaishi 1990, 64, 195.
22. Noyori., R., Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
23. Oguni, N., Omi, T. Tetrahedron Lett. 1984, 25, 2823.
24. Hursthouse, M.B., Motevaili, M., O'Brien, P., Walsh, J.R., Jones, A.C. J. Mater. Chem. 1991, 1, 139.
25. Soai, K., Watanabe, M., Koyano, M. Bull. Chem. Soc. Jpn. 1989, 62, 2124.
26. Kitamura, M., Suga, S., Kawai, K., Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071.
27. Chittenden, R.A., Cooper, C.H. J. Chem. Soc. C 1970, 49.
28. Beckett., A.H., Lan, N.T., McDonough, G.R. Tetrahedron 1969, 25, 5689.
29. Puchot, C., Samuel, O., Dunach, E., Zhao, S., Agami, C., Kagan, H.B. J. Am. Chem. Soc. 1986, 108, 2353.
30. Horeau, A., GuettS, J.P. Tetrahedron 1974, 30, 1923.
31. Wynberg, H., Feringa, B. Tetrahedron 1976, 32, 2831.
32. Kitamura, M., Okada, S., Suga, S., Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
33. Noyori, R., Suga, S., Kawai, K., Okada, S., Kitamura, M., Oguni, N., Hayashi, M., Kaneko, T., Matsuda, Y. J. Organomet. Chem. 1990, 382, 19.
34. Soai, K., Ookawa, A. J. Chem. Soc., Chem. Commun. 1986, 412.
35. Ookawa, A., Soai, K. J. Chem. Soc., Perkin Trans. 1 1987, 1465.
36. Soai, K., Ookawa, A., Ogawa, K., Kaba, T. J. Chem. Soc., Chem. Commun. 1987, 467.
37. Soai, K., Ookawa, A., Kaba, T., Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111.
38. Soai, K., Hirose, Y., Niwa, S. J. Fluorine Chem., in press.
39. Soai, K., Hirose, Y., Sakata, S. Bull. Chem. Soc. Jpn., in press.
40. Kobayashi, S., Murakami, M., Harada, T., Mukaiyama, T. Chem. Lett. 1991, 1341.
41. Okamoto., Y., Nakano, T., Ono, E., Hatada, K. Chem. Lett. 1991, 525.
42. Chelucci, G.,Falomi, M.,Giacomelli, G. Tetrahedron: Asymmetry 1990, 1, 843.
43. Asami, M., Inoue, S. Chem. Lett. 1991, 685.
44. Smaardijk, A.A., Wynberg, H. J. Org. Chem. 1987, 52, 135.
45. Wynberg, H. Asymmetric Catalysis by Cinchona Alkaloids. In Topics in Stereochemistry; Eliel, E.L., Wilen, S., Eds., Wiley-Interscience: New York, 1986; Vol. 16.
46. Muchow, G., Vannoorenberghe, Y., Buono, G. Tetrahedron Lett. 1987, 28, 6163.
47. Chaloner, P.A., Perera, S.A.R. Tetrahedron Lett. 1987, 28, 3013.
48. Chaloner, P.A., Langadianou, E. Tetrahedron Lett. 1990, 31, 5185.
49. Ookawa, A. Ph.D. Dissertation, Science University of Tokyo, 1987.
50. Corey, E.J., Naef, R., Hannon, F.J. J. Am. Chem. Soc. 1986, 108, 7114.
51. Corey, E.J., Hannon, F.J. Tetrahedron Lett. 1987, 28, 5233.
52. Corey, E.J., Hannon, F.J. Tetrahedron Lett. 1987, 28, 5237.
53. Soai, K., Nishi, M., Ito, Y. Chem. Lett. 1987, 2405.
54. Soai, K., Yokoyama, S., Ebihara, K., Hayasaka, T. J. Chem. Soc., Chem. Commun. 1987, 1690.
55. Soai, K., Yokoyama, S., Hayasaka, T. J. Org. Chem. 1991, 36, 4264.
56. Soai, K., Yokoyama, S., Hayasaka, T., Ebihara, K. J. Org. Chem. 1988, 53, 4148.
57. Soai., K., Hayasaka, T., Ugajin, S., Yokoyama, S. Chem. Lett. 1988, 1571.
58. Soai., K., Hayasaka, T., Ugajin, S. J. Chem. Soc., Chem. Commun. 1989, 516.
59. Soai., K., Okudo, M., Okamoto, M. Tetrahedron Lett. 1991, 32, 95.
60. Price, R.H. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed., Pergamon Press: Oxford, 1987; Chapter 56.1.
61. Johnson, W.S., Brinkmeyer, R.S., Kapoor, V.M., Yarnell, T.M. J. Am. Chem. Soc. 1977, 99, 8441.
62. Cohen., N., Lopresti, R.J., Neukom, C., Saucy, G. J. Org. Chem. 1980, 45, 582.
63. Oguni, N., Matsuda, Y., Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877.
64. Bolm, C., Zehnder, M., Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205.
65. Bolm, C., Ewald, M. Tetrahedron Lett. 1990, 31, 5011.
66. Tanaka, K., Ushio, H., Suzuki, H. J. Chem. Soc., Chem. Commun. 1989 1700
67. Pauling, H. Helv. Chim. Acta 1975, 58, 1781.
68. Corey, E.J., Yuen, P.-W., Hannon, F.J., Wierda, D.A. J. Org. Chem. 1990, 55, 784.
69. Soai, K., Watanabe, M., Yamamoto, A., Yamashita, T. J.Mol. Catal. 1991, 64, L27.
70. Watanabe, M., Araki, S., Butsugan, Y., Uemura, M. J. Org. Chem. 1991, 56, 2218.
71. Soai, K., Hayashi, H., Hasegawa, H. Heterocycles 1986, 24, 1287.
72. Soai, K., Niwa, S., Yamada, Y., Inoue, H. Tetrahedron Lett. 1987, 28, 4841.
73. Niwa, S., Soai, K. J. Chem. Soc., Perkin Trans. 1 1991, 2717.
74. Whitesell, J.K. Chem. Rev. 1989, 89, 1581.
75. Shono, T., Kise, N., Shirakawa, E., Matsumoto, H., Okazaki, E. J. Org. Chem. 1991, 56, 3063.
76. Soai, K., Watanabe, M. J. Chem. Soc., Chem. Commun. 1990, 43.
77. Rosini, C., Franzini, L., Pini, D., Salvadori, P. Tetrahedron: Asymmetry 1990, 1, 587.
78. Joshi, N.N., Srebnik, M., Brown, H.C. Tetrahedron Lett. 1989, 30, 5551.
79. Reetz, M.T., Steinbach, R., Wenderoth, B. Synth. Commun. 1981, 11, 261.
80. Yoshioka, M., Kawakita, T., Ohno, M. Tetrahedron Lett. 1989, 30, 1657.
81. Takahashi, H., Kawakita, T., Yoshioka, M., Kobayashi, S., Ohno, M. Tetrahedron Lett. 1989, 30, 7095.
82. Schmidt, B., Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 99.
83. Nakamura, A., Konishi, A., Otsuka, S. J. Chem. Soc., Dalton Trans. 1979, 488.
84. Ma, M.S., Angelici, R.J. Inorg. Chem. 1980, 19, 363.
85. Oguni, N., Omi, T., Yamamoto, Y., Nakamura, A. Chem. Lett. 1983, 841.
86. Mathur, N.K., Narang, C.K., Williams, R.E. Polymers as Aids in Organic Chemistry; Academic Press: New York, 1980.
87. Pittman, C.U. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed., Pergamon Press: Oxford, 1982; Chapter 55.
88. Kobayashi, N., Iwai, K. J. Polym. Sci., Polym. Chem. Ed. 1980, 18, 923.
89. Tsuboyama., S. Bull. Chem. Soc. Jpn. 1966, 39, 698.
90. Soai, K., Niwa, S., Watanabe, M. J. Org. Chem. 1988, 53, 927.
91. Niwa, S. Ph.D. Dissertation, Science University of Tokyo, 1991.
92. Soai, K., Niwa, S., Watanabe, M. J. Chem. Soc., Perkin Trans. 1 1989, 109.
93. Soai, K., Watanabe, M. Tetrahedron: Asymmetry 1991, 2, 97.
94. Itsuno, S., Frechet, J.M.J. J. Org. Chem. 1987, 52, 4140.
95. Itsuno, S., Sakurai, Y., Ito, K., Maruyama, T., Nakamura, S., Frfechet, J.M.J. J. Org. Chem. 1990, 55, 304.
96. Watanabe, M., Araki, S., Butsugan, Y., Uemura, M. Chem. Express 1990, 5, 761.
97. Posner, G.H. Angew. Chem., Int. Ed. Engl. 1978, 1, 7, 487.
98. Carpino, L., Mansour, E.M.E., Cheng, C.H., Williams, J.R., MacDonald, R., Knapczyk, J., Carman. Acc. Chem. Res. 1987, 20, 40.
99. Soai, K., Watanabe, M., Yamamoto, A. J. Org. Chem. 1990, 55, 4832.
100. Niwa, S., Soai, K. J. Chem. Soc., Perkin Trans. 1 1990, 937.
101. Tombo, G.M.R., Didier, E., Loubinoux, B. Synlett 1990, 547.
102. Oppolzer, W., Radinov, R.N. Tetrahedron Lett. 1988, 29, 5645.
103. Oppolzer, W., Radinov, R.N. Tetrahedron Lett. 1991, 32.
104. Klein, H., Steinmetz, A. Tetrahedron Lett. 1975, 4249.
105. Kogure., T., Eliel, E.L. J. Org. Chem. 1984, 49, 576.
106. Seebach, D., Beck, A.K., Roggo, S., Wonnacott, A. Chem. Ber. 1985, 118, 3673.
107. Soai, K., Kawase, Y., Oshio, A. J. Chem. Soc., Perkin Trans. 1 1991, 1613.
108. Hubscher, J., Barner, R. Helv. Chim. Acta 1990, 73, 1068.
109. Pilul, S., Raczko, J., Ankner, K., Jurczak, J. J. Am. Chem. Soc. 1987, 109, 3981.
110. DeShong., P., Waltermine, R.E., Ammon, H.L. J. Am. Chem. Soc. 1988, 110, 1901.
111. Yamaguchi., Y., Tatsuta, N., Hayakawa, K., Kanematsu, K. J. Chem. Soc., Chem. Commun. 1989, 470.
112. Martin., S.F., Guinn, D.E. J. Org. Chem. 1987, 52, 5588.
113. DeShong., P., Lin, M.-T., Perez, J.J. Tetrahedron Lett. 1986, 27, 2091.
114. Ziegler., F.E., Wester, R.T. Tetrahedron Lett. 1984, 25, 617.
115. Mori., K., Kisida, H. Tetrahedron 1986, 42, 5281.
116. Sammes., P.G., Thetford, D. J. Chem. Soc., Perkin Trans. 1 1988, 111.
117. Drueckhammer, D.G., Barbas, C.F., Nozaki, K., Wong, C.-H., Wood, C.Y., Ciufolini, M.A. J. Org. Chem. 1988, 53, 1607.
118. Suzuki, K.,Yuki, Y., Mukaiyama, T. Chem. Lett. 1991, 1529.
119. Raczko., J., Golebiowski, A., Krajewski, J.W., Gluzinski, P., Jurczak, J. Tetrahedron Lett. 1990, 31, 3797.
120. Soai, K., Kawase, Y. J. Chem. Soc., Perkin Trans. 1 1990, 3214.
121. Furstner, A. Synthesis 1989, 571.
122. GuettS, M., Capillon, J., Guette, J.-P. Tetrahedron 1973, 29, 3659.
123. Soai, K., Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781.
124. Soai, K., Yokoyama, S., Hayasaka, T., Ebihara, K. Chem. Lett. 1988, 843.
125. Saucy, G., Borer, R. Helv. Chim. Acta 1971, 54, 2121-2217.
126. Rosenberger, M., Borer, R., Saucy, G. J. Org. Chem. 1978, 43, 1550.
127. Smith, L.R., Williams, H.J., Silverstein, R.M. Tetrahedron Lett. 1978 3231
128. Yamamoto, Y., Yamada, J. J. Am. Chem. Soc. 1987, 109, 4395.
129. Maruoka, K., Araki, Y., Yamamoto, H. Tetrahedron Lett. 1988, 29, 3101.
130. Kauffmann, T., Antfang, E., Ennen, B., Klas, N. TetrahedronLett. 1982, 23, 2301.
131. Kauffmann., T.,Pahde, C., Wingbermuhle, D. Tetrahedron Lett. 1985, 26, 4059.
132. Kauffmann., T., Pahde, C., Tannert, A., Wingbermuhle, D. Tetrahedron Lett. 1985, 26, 4063.
133. Reetz, M.T., Westennann, J., Steinbach, R., Weneroth, B., Peter, R., Ostarek, R., Maus, S. Chem. Ber. 1985, 118, 1421.
134. Okude, Y., Hirano, S., Hiyama, T., Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179.
135. Wada, M., Ohki, H., Akiba, K. Tetrahedron Lett. 1986, 27, 4771.
136. Soai, K., Watanabe, M., Koyano, M. J. Chem. Soc., Chem. Commun. 1989, 534.
137. Midland, M.M., Lee, P.E. J. Org. Chem. 1981, 46, 3934.
138. Kluge., A.F., Kertesz, D.J., OYang, C., Wu, H.Y. J. Org. Chem. 1987, 52, 2860.
139. Johnson., W.S., Frei, B., Gopalan, A.S. J. Org. Chem. 1981, 46, 1512.
140. Mukaiyama., T., Suzuki, K. Chem. Lett. 1980, 255.
141. Vigneron., J.P., Blauchard, J.M. Tetrahedron Lett. 1980, 21, 1739.
142. Noyori, R.,Tomino, I.,Yamada, M.,Nishizawa, M.J.Am. Chem. Soc. 1984, 106, 6717.
143. Cho, B.T., Park, W.S. Bull. Korean Chem. Soc. 1987, 8, 257 and references cited therein.
144. Mukaiyama, T., Suzuki, K., Soai, K., Sato, T. Chem. Lett. 1979, 447.
145. Ishihara, K., Mori, A., Arai, I., Yamamoto, H. Tetrahedron Lett. 1986, 26, 983.
146. Soai, K., Niwa, S. Chem. Lett. 1989, 481.
147. Kitano, Y., Matsumoto, T., Okamoto, S., Shimazaki, T., Kobayashi, Y., Sato, F. Chem. Lett. 1987, 1523.
148. Suzuki., M., Yanagisawa, A., Noyori, R. J. Am. Chem. Soc. 1988, 110, 4718.
149. Johnson., C.R., Penning, T.D. J. Am. Chem. Soc. 1988, 110, 4726.
150. Fried., J., Lin, C., Mehra, M., Kao, W., Dalven, P. Ann. N.Y. Acad. Sci. 1971, 180, 38.
151. Masamune, S., Hirama, M., Mori, M., Ali, S.A., Garvey, D.A. J. Am. Chem. Soc. 1981, 103, 1568.
152. Zentel, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 1407.
153. Eidenschink, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 1424.
154. Mukaiyama, T., Iwasawa, N. Chem. Lett. 1982, 1903.
155. Iwasawa., N., Mukaiyama, T. Chem. Lett. 1983, 297.
156. Soai, K., Hori, H., Kawahara, M. Tetrahedron: Asymmetry 1990, 1, 769.
157. Soai, K., Kawase, Y., Niwa, S. Heterocycles 1989, 29, 2219.
158. Van Oeveren, A., Menge, W., Feringa, B.L. Tetrahedron Lett. 1989, 30, 6427.
159. Hayashi, M., Kaneko, T., Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 25.
160. Uskokovic, M.R., Lewis, R.L., Partridge, J.J., Despreaux, C.W., Pruess, D.L. J. Am. Chem. Soc. 1979, 101, 6742.
161. Frank, A., Ruchardt, C. Chem. Lett. 1984, 1431.
162. Salz., U., Ruchardt, C. Chem. Ber. 1984, 117, 3457.
163. Ferles, M., Stern, P., Trska, P. Collect. Czech. Chem. Commun. 1974, 39, 3317.
164. Imuta, M., Ziffer, H. J. Org. Chem. 1978, 43, 3530.
165. Takeshita., M., Terada, K., Akutsu, N., Yoshida, S., Sato, T. Heterocycles 1987, 26, 3051.
166. Ohno, A., Nakai, J., Nakamura, N., Goto, T., Oka, S. Bull. Chem. Soc. Jpn. 1981, 54, 3482.
167. Schmidt., M., Amstutz, R., Crass, G., Seebach, D. Chem. Ber. 1980, 113, 1691.
168. Samaddar., A.K., Konar, S.K., Nasipuri, D. J. Chem. Soc., Perkin Trans. 1 1983, 1449.
169. Seki., M., Baba, N., Oda, J., Inouye, Y. J. Org. Chem. 1983, 48, 1370.
170. Midland., M.M., McLoughlin, J.I. J. Org. Chem. 1984, 49, 1316.
171. Soai, K., Hori, H., Niwa, S. Heterocycles 1989, 29, 2065.
172. Soai, K., Hori, H., Kawahara, M. J. Chem. Soc., Chem. Commun. 1992, 106.
173. Barton, D.H.R., de Vries, J.X. J. Chem. Soc. 1963, 1916.
174. Elander, M., Leander, K., Luning, B. Acta Chem. Scand. 1969, 23, 2177.
175. Asami, M., Mukaiyama, T. Chem. Lett. 1980, 17.
176. Alexakis., A., Sedrani, R., Normant, J.F., Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283.
177. Commercon., M., Mangeney, P., Tejero, T., Alexakis, A. Tetrahedron: Asymmetry 1990, 1, 287.
178. Olivero., A.G.; Weidmann, B., Seebach, D. Helv. Chim. Acta 1981, 64, 2485.
179. Meyers., A.I., Hanagan, M.A., Trefonas, L.M., Baker, R.J. Tetrahedron 1983, 39, 1991.
180. Soai, K., Hori, H., Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253.
181. Morrison, J.D., Mosher, H.S. Asymmetric Organic Reactions; Prentice-Hall: New York, 1971.
182. Eliel., E.L. In Asymmetric Synthesis; Morrison, J.D., Ed., Academic Press: New York, 1983; Vol. 2A, Chapter 5.
183. Bartlett., P.A. Tetrahedron 1980, 36, 3.
184. Cram, D.J., Elhafez, F.A.A. J. Am. Chem. Soc. 1952, 74, 5828.
185. Cherest., M., Felkin, H., Prudent, N. Tetrahedron Lett. 1968, 2199.
186. Reetz, M.T., Kyung, S.H., Hullmann, M. Tetrahedron 1986, 42, 2931.
187. Matsuzaka., S., Isaka, M., Nakamura, E., Kuwajima, I. Tetrahedron Lett. 1989, 30, 1975.
188. Yamamoto., Y., Yamada, J. J. Am. Chem. Soc. 1987, 109, 4395.
189. Maruoka., K., Itoh, T., Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 4573.
190. Yamamoto., Y., Maruyama, K. J. Am. Chem. Soc. 1985, 107, 6411.
191. Soai, K., Niwa, S., Hatanaka, T. Bull. Chem. Soc. Jpn. 1990, 63, 2129.
192. Jones, P.R., Goller, E.J., Kauffman, W.J. J. Org. Chem. 1971, 36, 3311.
193. Soai, K., Niwa, S., Hatanaka, T. J. Chem. Soc., Chem. Commun. 1990, 709.
194. Niwa, S., Hatanaka, T., Soai, K. J. Chem. Soc., Perkin Trans. 1 1991, 2025.
195. Soai, K., Hatanaka, T., Yamashita, T. 61st National Meeting of the Chemical Society of Japan, Yokohama, 1991; Paper 2D1 28; J. Chem. Soc., Chem. Commun., in press.
196. Reetz, M.T., Jung, A. J. Am. Chem. Soc. 1983, 105, 4833.
197. Hayashi, M., Miwata, H., Oguni, N. Chem. Lett. 1989, 1696.
198. Hayashi, M., Miwata, H., Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 1167.
199. Wynberg, H. Chimia 1989, 43, 150.
200. Soai, K., Niwa, S., Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982
201. Alberts, A.H., Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265.