Ambiphilic allenyl enolates

Tetrahedron

Volumn 53, Issue 30, 1997, Pages 10197-10227

  Fredrick, Mark A ^a,b,c   Hulce, Martin ^a,d,e,f  

^a CREIGHTON UNIVERSITY   (United States)

^b NEBRASKA WESLEYAN UNIVERSITY   (United States)

^c MICHIGAN STATE UNIVERSITY   (United States)

^d BUTLER UNIVERSITY   (United States)

^e JOHNS HOPKINS UNIVERSITY   (United States)

^f DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOIC ACID; ALKENE DERIVATIVE; ALKYNE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030738245     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00389-X     Document Type: Review

References (192)

1. Perlmutter, P. Conjugate Addition Reaction in Organic Synthesis; Pergamon Press: Oxford, 1992.
2. Claisen, L.; Komnenos, T. Liebigs Ann. Chem. 1883, 218, 158.
3. Claisen, L. J. Prakt. Chem. 1887, 35, 413.
4. Michael, A. Am. Chem. J. 1887, 9, 112.
5. Bergmann, E.D.; Ginsburg, D.; Pappo, R. Org. React. 1959, 10, 179.
6. House, H.O. Modern Synthetic Reactions; 2nd ed, W.A. Benjamin: Menlo Park, 1972, pp. 595-623.
7. Organocopper Reagents: A Practical Approach; Taylor, R.J.K., Ed., Oxford University Press: Oxford, 1994.
8. Lipshutz, B.H.; Sengupta, S. Org. React 1992, 41, 135.
9. Kozlowski, J.A. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I., Eds., Pergamon Press: Oxford, 1991, Vol. 4, Ch. 1.4.
10. Posner, G.H. Org. React. 1972, 19, 1.
11. Colvin, E.W. Silicon Reagents in Organic Synthesis; Academic Press: New York, 1988.
12. (a) Piers, E.; Roberge, J.Y. Tetrahedron Lett. 1991, 32, 5219.
13. (b) Piers, E.; Morton, H.E.; Chong, J.M. Can. J. Chem. 1987, 65, 78.
14. Nishida, M.; Nishida, A.; Kawahara N. J. Org. Chem. 1996, 61, 3574.
15. Spitzner, D. In Studies in Natural Products Chemistry; Rahman, A., Ed., Elsevier: Amsterdam, 1991, Vol. 8 (Part E), pp. 409-431.
16. Posner, G.H. Chem. Rev. 1986, 86, 831.
17. Galway, R.E.; Synthesis 1976, 777.
18. Hulce, M.; Chapdelaine, M.J. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I., Eds., Pergamon Press: Oxford, 1991, Vol. 4, Ch. 1.6.
19. Noyori, R.; Suzuki, M. Chemtracts 1990, 173.
20. For a recent example: Snider, B.B.; Vo, N.H.; O'Neil, S.V.; Foxman, B.M. J. Am. Chem. Soc. 1996, 118, 7644.
21. Chapdelaine, M.J.; Hulce, M. Org. React. 1990, 38, 225.
22. Hulce, M. In Studies in Natural Products Chemistry; Rahman, A., Ed., Elsevier: Amsterdam, 1992, Vol. 10 (Part F), pp. 147-199.
23. (a) Kohler, E.P.; Butler, F.R. J. Am. Chem. Soc. 1926, 48, 1036.
24. (b) Farmer, E.M.; Mehta, T.N. J. Chem. Soc. 1931, 1904.
25. (c) Ames, D.E.; Bowman, R.E. J. Chem. Soc. 1950, 329.
26. (a) Saito, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 2928.
27. (b) Lohray, B.B.; Jayachandran, B.; Bhushan, V.; Nandanan, E.; Ravindranathan, T. J. Org. Chem. 1995, 60, 5983.
28. (c) Lui, H.; Gayo, L.M.; Sullivan, R.W.; Choi, A.Y.H. Moore, H.W. J. Org. Chem. 1994, 59, 3284.
29. (d) Yanagita, M.; Inayama, S.; Hirakura, M.; Seki, F. J. Org. Chem. 1958, 23, 690.
30. (e) Campbell, J.A.; Babcock, J.C. J. Am. Chem. Soc. 1959, 81, 4069.
31. (f) Irie, H.; Mizuno, Y.; Taga, T.; Osaki, K. J. Chem. Soc., Perkin Trans. I 1982, 25.
32. (g) LaFontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460.
33. (h) Utimoto, K.; Wakabayashi, Y.; Horiie, T.; Inoue, M.; Shishiyama, Y.; Obayashi, M.; Nozaki, H. Tetrahedron 1983, 39, 967.
34. (i) Bigorra, J.; Font, J.; Ortuna, R.M.; Sanchez-Ferrando, F.; Florencio, F.; Martinez-Carrera, S.; Garcia-Blanco, S. Tetrahedron 1985, 41, 5577, 5589.
35. (j) Seijas, J.A.; Vázquez-Tato, M.P.; Castedo, L.; Estévez, R.J.; Ruíz, M. J. Org. Chem. 1992, 57, 5283.
36. For examples of acid-catalyzed 1,6 additions: (a) Kuo, Ch.H.; Taub, D.; Wendler, N.L. J. Org. Chem. 1968, 33, 3126.
37. (b) Darvesh, S.; Grant, A.S.; MaGee, D.I.; Valenta, Z. Can. J. Chem. 1989, 67, 2237.
38. (a) Bloom, J.; Ingold, C.K. J. Chem. Soc. 1931, 2765.
39. (b) Marshall, J.A.; Ruden, R.A.; Hirsch, L.K.; Phillipe, M. Tetrahedron Lett. 1971, 3795.
40. (c) Marshall, J.A.; Roebke, H. J. Org. Chem. 1966, 31, 3109.
41. (a) Tamaru, Y.; Harada, T.; Iwamoto, H.; Yoshida, Z. J. Am. Chem. Soc. 1978, 100, 5221.
42. (b) Marshall, J.A.; Audia, J.E.; Shearer, B.G. J. Org. Chem. 1986, 51, 1730.
43. (c) Cooke, M.P. Gooswami, R. J. Am. Chem. Soc. 1977, 99, 642.
44. Kaswamata, T.; Harimaya, K.; Inamyama, S. Bull. Chem. Soc. Japan 1988, 61, 3770.
45. Farmer, E.H.; Martin, S.R.W. J. Chem. Soc. 1933, 960.
46. (a) Brocchini, S.J.; Eberle, M.; Lawton, R.G. J. Am. Chem. Soc. 1988, 110, 5211.
47. (b) Barbot, F.; Kadib-Elban, A.; Miginiac, P. J. Organomet. Chem. 1988, 345, 239.
48. (c) Machiguchi, T.; Wada, Y.; Hasegawa, T.; Yamabe, S.; Minato, T.; Nozoe, T. J. Am. Chem. Soc. 1985, 117, 1258.
49. Biggora, J.; Font, J.; Jaime, C.; Ortuno, R.M.; Sanchez-Ferrando, F. Tetrahedron 1989, 72, 5577.
50. (a) Li, V.S.; Choi, D.; Tang, M.S.; Kohn, H. J. Am. Chem. Soc. 1996, 118, 3765.
51. (b) Kumar, M.; Lee, S.J.; Cassady, J.M.; Hurley, L.H. J. Am. Chem. Soc. 1996, 118, 9209.
52. (c) Schkerynatz, J.; Danishefsky, S.J. Synlett 1995, 475.
53. (d) For an application to the design and synthesis of an endiyne prodrug: Shair, M.D.; Yoon, T.Y.; Mosny, K.K.; Chou, T.C.; Danishefsky, S.J. J. Am. Chem. Soc. 1996, 118, 9509.
54. (a) McMorris, T.C.; Kelner, M.J.; Wang, W.; Diaz, M.A.; Estes, L.A.; Taetle, R. Experientia 1996, 52, 75.
55. (b) McMorris, T.C.; Hu, Y.; Keiner, M.J. J. Chem. Soc. Chem. Commun, 1997, 315.
56. (a) Armstong, R.W.; Moran, E.J. J. Am. Chem. Soc. 1992, 114, 371.
57. (b) Bryant, H.J.; Dardonville, C.Y.; Hodgkinson, T.J.; Shipman, M.; Slawin, A.M.Z. Synlett 1996, 973.
58. (a) Boger, D.L.; Garbaccio, R.M. Bioorg. Med. Chem. 1997, 5, 263.
59. (b) Boger, D.L.; Han, N.; Tarby, C.M.; Boyce, C.W.; Cai, H.; Jin, Q.; Kitos, P.A. J. Org. Chem. 1996, 61, 4894.
60. (c) Boger, D.L.; McKie, J.A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. 1996, 118, 2301.
61. (d) Boger, D.L.; McKie, J.A.; Cai, H.; Cacciari, B.; Baraldi, P.G. J. Org. Chem. 1996, 61, 1710.
62. (e) Boger, D.L.; Mēsini, P. J. Am. Chem. Soc. 1995, 117, 11647.
63. (f) for applications to the design of DNA-DNA interstrand cross-linking reagents:
64. (i) Park, H.J.; Kelly, R.C.; Hurley, L.H. J. Am. Chem. Soc. 1996, 118, 10041.
65. (ii) Seaman, F.C.; Hurley, L. J. Am. Chem. Soc. 1996, 118, 10052.
66. Kushida, T.; Uesugi, M.; Sugiwa, Y.; Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Ojika, M.; Ymada, K. J. Am. Chem. Soc. 1994, 116, 479.
67. (a) Barrett, A.G.M.; Hamprecht, D.; White, A.J.P.; Williams, D.J. J. Am. Chem. Soc. 1996, 118, 7863.
68. (b) Barrett, A.G.M.; Kasdorf, K. J. Am. Chem. Soc. 1996, 118, 11030.
69. (c) Charette, A.B.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327.
70. (d) Falk, J.R.; Mekonnen, B.; Yu, J.; Lai, J.Y. J. Am. Chem. Soc. 1996, 118, 6096.
71. Grieco, P.A.; Finkelhor, R. J. Org. Chem. 1973, 38, 2100.
72. Danishefsky, S.; Rovnyak, G.; Cavanaugh, R. J. Chem. Soc., Chem. Commun. 1969, 636.
73. For leading references: (a) Shair, M.D.; Yoon, T.Y.; Mosny, K.K.; Chou, T.C.; Danishefsky, S.J. J. Am. Chem. Soc. 1996, 118, 9505.
74. (b) De Voss, J.J.; Hangemand, J.J.; Townsend, C.A. J Org. Chem. 1994, 59, 2715.
75. (a) Myers, A.G.; Arvedson, S.P.; Lee, R.W. J. Am. Chem. Soc. 1996, 118, 4725.
76. (b) Myers, A.G.; Cohen, S.B.; Kwon, B.M. J. Am. Chem. Soc. 1994, 116, 1670.
77. Hirama, M.; Tokuda, M.; Fujiwara, K. Synlett 1991, 651.
78. (a) Toshima, K.; Ohta, K.; Yanagawa, K.; Kano, T.; Nakata, M.; Kinoshita, M.; Matsumura, S. J. Am. Chem. Soc. 1995, 117, 10825.
79. (b) Lamothe, M. Fuchs, P.L. J. Am. Chem. Soc. 1993, 115, 4483.
80. Niclolaou, K.C.; Maligres, P.; Suzuki, T.; Wendeborn, S.V.; Dai, W.M.; Chadha, R.K. J. Am. Chem. Soc. 1992, 114, 8890.
81. Magnus, P.; Eisenbeis, S.A.; Rose, W.,C.; Zein, W.C.; Solomon, W. J. Am. Chem. Soc. 1993, 115, 12627.
82. Bowden, K.; Braude, E.A.; Jones, E.R.H.; Weedon, B.C.L. J. Chem. Soc. 1946, 45.
83. Bennani, Y.L. J. Org. Chem. 1996, 61, 3542.
84. Kraus, N.; Hohmann, M. Synlett 1996, 89.
85. Genus, J.F.; Peters, D.D.; Bryson, T.A. Synlett 1993, 759.
86. (a) Daniel, D.; Middleton, R.; Henry, H.L. Okamura, W.H. J. Org. Chem. 1996, 61, 5617.
87. (b) von Bilinski, V.; Karpf, M.; Dreiding, A.S. Helv. Chem. Acta 1986, 69, 1734.
88. Molander, G.A.; Brown, H.C. J. Org. Chem. 1977, 42, 3106.
89. (a) Trost, B.M.; McIntosh, M.C. J. Am. Chem. Soc. 1995, 117, 7255.
90. (b) Jeffery, T. Synthesis 1987, 70.
91. (c) Jeffery, T. Synth. Commun. 1988, 77.
92. Krause, N. Chem. Ber. 1990, 123, 2173.
93. JanakiramRao, C.; Knochel, P. J. Org. Chem. 1991, 56, 4593.
94. Cheng, M.; Hulce, M. J. Org. Chem. 1990, 55, 964.
95. Nakatani, K.; Arai, K.; Hirayama, N.; Matsuda, F.; Terashima, S. Tetrahedron Lett. 1990, 31, 2323.
96. Rathjen, H.J.; Margaretha, P.; Wolff, S.; Agosta, W.C. J. Am. Chem. Soc. 1991, 113, 3904.
97. (a) Lee, A.S.; Norman, A.W.; Okamura, W.H. J. Org. Chem. 1992, 57, 3846.
98. (b) Enas, J.D.; Shen, G.Y.; Okamura, W.H. J. Am. Chem. Soc. 1991, 113, 3873.
99. Nakamura, T.; Namiki, M.; Ono, K. Chem. Pharm. Bull. 1987, 35, 2635.
100. Brandsma, L. Preparative Acetylenic Chemistry; 2nd ed, Elsevier: Amsterdam, 1988, pp. 102-103.
101. Trost, B.M.; Chan, C.; Ruhter, G. J. AM. Chem. Soc. 1987, 109, 3486.
102. Trost, B.M.; Mastubara, S.; Caringi, J.J. J. Am. Chem. Soc. 1989, 111, 8745.
103. Haubrich, A.; van Klaveren, M.; van Koten, G.; Handke, G.; Krause, N. J. Org. Chem. 1993, 58, 5849.
104. 2: C, 71.03; H, 7.95. Found C, 70.91; H, 7.94.
105. Brandsma, L. Preparative Acetylenic Chemistry; 2nd ed, Elsevier: Amsterdam, 1988, pp. 101, 105-106.
106. Typically, nucleophilic addtions of thiolates to simple alkynes are anti additions, leading to (E)-thioenol ethers. Propiolates, on the other hand, are less stereoselective, and often syn addition predominates: (a) Eliel, E.L.; Wilen, S.H. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994, p. 557.
107. (b) Rutledge, T.F. Acetylenes and Allenes; Reinhold: New York, 1969, pp. 170-171; 233-234.
108. Krause, N. J. Org. Chem. 1992, 57, 3509.
109. Amos, R.A.; Katzenellenbogen, J.A.; J. Org. Chem. 1978, 43, 555.
110. Tsuboi, S.; Sakamoto, J.; Kuroda, A.; Utaka, M.; Takeda, A. Bull. Chem. Soc. Japan 1988, 61, 1410.
111. Gschwend, H.W.; Rodriguez, H.R. Org. React. 1979, 26, 1.
112. Griffen, E.J.; Roe, D.G.; Snieckus, V. J. Org. Chem. 1995, 60, 1484 and references therein.
113. Lee, S.H.; Hulce, M. Synlett 1992, 485.
114. Ritter, K. Synthesis 1993, 735.
115. Krause, N. Chem. Ber. 1991, 124, 2633.
116. Handke, G.; Krause, N. Tetrahedron Lett. 1993, 34, 6037.
117. Knotter, D.M.; van Maanen, H.L.; Grove, D.M.; Spek, A.L.; van Koten, G. Inorg. Chem. 1991, 30, 3309.
118. (a) Schuster, H.F.; Coppola, G.M. Allenes in Organic Synthesis; Wiley-Interscience: New York, 1984, p. 27.
119. (b) Wipf, P.; Fritch, P.C. J. Org. Chem. 1994, 59, 4875.
120. (c) Amos, R.A.; Katzenellenbogen, J.A. J. Org. Chem. 1977, 42, 2537.
121. (d) Dollat, J.M.; Luche, J.L.; Crabbé, P. J. Chem. Soc., Chem. Commun. 1977, 761.
122. (e) Baret, P.; Barreiro, E.; Greene, A.E.; Luche, J.L.; Teixeira, M.A.; Crabbé, P. Tetrahedron 1979, 2931.
123. (f) Anderson, S.J.; Hopkins, W.T.; Wigal, CT. J. Org. Chem. 1992, 57, 4304.
124. (g) Mu, Y.; Gibbs, R.A.; Eubanks, L.M.; Poulter, C.D. J. Org. Chem., 1996, 61, 8010.
125. Nakamura, E. in Organocopper Reagents: A Practical Approach; Taylor, R.J.K., Ed., Oxford University Press: Oxford, 1994, ch. 6.
126. Hulce, M. Abstracts of Papers, 26th Midwestern Regional Meeting of the American Chemical Society, Omaha, NE, 1991; ORGN 134.
127. (a) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J.F. Tetrahedron 1991, 47, 1677.
128. (b) Marek, I.; Mangeney, P.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1986, 27, 5499.
129. (c) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J.F. Tetrahedron Lett. 1989, 30, 2387; 2391.
130. (d) Mitani, M.; Matsumoto, H.; Gouda, N.; Koyama, K. J. Am. Chem. Soc. 1990, 112, 1286.
131. (a) Petragnani, N.; Yonashiro, M. Synthesis 1982, 521.
132. (b) Yamamoto, Y.; Hatsuya, S.; Yamada, J. Tetrahedron Lett. 1989, 30, 3445.
133. (c) Fan, R.; Hudlicky, T. Tetrahedron Lett. 1989, 30, 5533.
134. (d) Hudlicky, T.; Maxwell, M.H., Jr. Synth. Commun. 1989, 19, 1847.
135. (e) Yamamoto, Y.; Hatsuya, S.; Yamada, J. J. Chem. Soc., Chem. Commun. 1988, 86; 1639.
136. (f) Büchi, G.; Wüest, H. J. Am. Chem. Soc. 1974, 96, 7573.
137. (g) Parra, M.; Mestres, R.; Aparicio, D.; Durana, N.; Rubiales, G. J. Chem. Soc., Chem. Commun. 1989, 327.
138. (h) Seebach, D.; Misslitz, U.; Uhlmann, P. Angew. Chem. Int. Ed. Engl. 1989, 28, 472.
139. (i) Petasis, N.A.; Teets, K.A. J. Am. Chem. Soc. 1992, 114, 10328.
140. (j) van Maanen, H.L.; Kleijn, H.; Jastrzebski, J.T.B.H.; Lakin, M.T.; Spek, A.L.; van Koten, G. J. Org. Chem. 1994, 59, 7839.
141. (k) Smith, M.K.; Semerad, C.L.; Berkowitz, D.B. Abstracts of Papers, 31st Midwestern Regional Meeting of the American Chemical Society, Sioux Falls, SD, 1996; ORGN 71.
142. Arndt, S.; Handke, G.; Krause, N. Chem. Ber. 1993, 126, 251. For a related use of BHT to enhance diastereoselection of protonation of a dianion: Stork, G.; West, F.; Lee, H.Y.; Issacs, R.C.A.; Manabe, S. J. Am. Chem. Soc. 1996, 118, 10660.
143. Arndt, S.; Handke, G.; Krause, N. Chem. Ber. 1993, 126, 251. For a related use of BHT to enhance diastereoselection of protonation of a dianion: Stork, G.; West, F.; Lee, H.Y.; Issacs, R.C.A.; Manabe, S. J. Am. Chem. Soc. 1996, 118, 10660.
144. Lee, S.H.; Shih, M.J.; Hulce, M. Tetrahedron Lett. 1992, 33, 185.
145. (a) Rathke, M.W.; Sullivan, D. Tetrahedron Lett. 1972, 4249.
146. (b) Malhotra, S.K.; Ringold, H.J. J. Am. Chem. Soc. 1963, 85, 1538.
147. (c) Ringold, J.H.; Malhotra, S.K. Tetrahedron Lett. 1962, 669.
148. Krause, N.; Wagner, R.; Gerold, A. J. Am. Chem. Soc. 1994, 116, 381.
149. Laux, M.; Krause, N.; Koop, U. Synlett 1996, 87.
150. Lee, S.H. Reactions ofAmbiphilic Cyclic Allenyl Enolates and Enol Trifluoromethanesulfonates as Enolate Equivalents, University of Maryland Baltimore County 1992.
151. Krause, N.; Hohmann, M. Synlett 1996, 89.
152. For an alternative approach to generate y-selectivity in dienolates: (a) Schlessinger, R.H.; Mjalli, A.M.M.; Adams, A.D.; Springer, J.P.; Hoogsteen, K. J. Org. Chem. 1992, 57, 2992.
153. (b) Iqbal, J.; Kahn, M.A. Synth. Commun. 1989, 19, 515.
154. (c) Iqbal, J.; Mohan, R. Tetrahedron Lett. 1989, 30, 239.
155. (d) Dellassoued, M.; Ennigrou, R.; Gaudemar, M. J. Organomet. Chem. 1988, 338, 149.
156. Eliel, E.L.; Wilen, S.H. Stereochemistry of Organic Compounds; Wiley-Interscience, 1994, pp. 913-919.
157. (a) Colvin, E.W. Silicon Reagents in Organic Synthesis; Academic Press: New York, 1988, p.106.
158. (b) Binkley, E.S.; Heathcock, C.H. J. Org. Chem. 1975, 40, 2156.
159. (c) Snider, B.B.; Yang, K. J. Org. Chem. 1992, 57, 3615.
160. (d) Stork, G.; Hurdlik, P.F. J. Am. Chem. Soc. 1968, 90, 4464.
161. Black, T.H. Org. Prep. Proc. Int. 1989, 21, 179.
162. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: New York, 1992, pp. 41-42.
163. 1H NMR δ 5.92 (q, 1H, J=6.2 Hz), 2.45 (br s, 4H), 1.56 (d, 3H, J=6.2 Hz), 1.54 (t, 3H, J=1.4 Hz), 0.08 (s, 9H). NOE difference spectroscopy established both regiochemistry and stereochemistry of silylation: upon irradiation of the δ 0.08 singlet, a substantial enhancement of the δ 1.56 doublet was observed.
164. (a) Suzuki, M.; Yanagisawa, A.; Noyori, R. J. Am. Chem. Soc. 1985, 107, 3348.
165. (b) Tardella, P.A. Tetrahedron Lett. 1969, 1117.
166. (c) Nishiyama, H.; Sakuta, K.; Itoh, K. Tetrahedron Lett. 1984, 25, 223; 2487.
167. (a) Ritter, K. Synthesis 1993, 735.
168. (b) Dieter, R.K.; Dieter, J.W.; Alexander, C.W.; Bhinderwala, N.S. J. Org. Chem. 1996, 61, 2930.
169. Krause, N.; Arndt, S. Chem. Ber. 1993, 126, 261.
170. For a complementary isomerization of 5-choro-2,3-alkadienones to 3-chloro-2,4-alkadienones: Santelli-Rouvier, C.; Lefrère, S.; Santelli, M. J. Org. Chem. 1996, 61, 6678.
171. (a) Kleijn, H.; Eijsinga, H.; Westmijze, H.; Meijer, J.; Vermeeer, P. Tetrahedron Lett. 1976, 947.
172. (b) Alexakis, A.; Normant, J.F. Isr. J. Chem. 1984, 24, 113.
173. (c) Koosha, K.; Berlain, J.; Capmau, M.L.; Chodkiewicz, W. Bull. Soc. Chim. France 1975, 1284; 1291.
174. (d) Lipshutz, B.H. Synlett 1990, 119.
175. (e) Lipshutz, B.H.; Wilhelm, R.S.; Kozlowski, J.A. Tetrahedron 1984, 40, 5005.
176. (f) Chen, H.M.; Oliver, J.P. J. Organomet. Chem. 1986, 316, 255.
177. (g) Berlain, J.; Baltioni, J.P.; Koosha, K. Bull. Soc. Chim. France II 1979, 183.
178. (a) Fleming, I.; Pulido, F.J. J. Chem. Soc., Chem. Commun. 1986, 1010.
179. (b) Fleming, I.; Rowley, M.; Cuadrado, P.; Gonzalez-Nogal, A.M.; Pulido, F.J. Tetrahedron 1989, 45, 413.
180. (c) Cuadro, P.; Gonzalez-Nogal, A.M.; Pulido, F.J.; Fleming, I. Tetrahedron Lett. 1988, 29, 1825.
181. Kowalski, C.J.; Weber, A.E.; Fields, K.W. J. Org. Chem. 1982, 47, 5088.
182. Lee, S.H.; Hulce, M. Tetrahedron Lett. 1990, 31, 311.
183. (a) Marino, J.P.; Linderman, R.J. J. Org. Chem. 1981, 46, 3696.
184. (b) Posner, G.H.; Whitten, C.E.; Sterling, J.J.; Brunelle, D.J. Tetrahedron Lett. 1974, 2591.
185. Krause, N. Liebigs Ann. Chem. 1993, 521.
186. (a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K.N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
187. (b) Alexakis, A. In Organocopper Reagents: A Practical Approach; Taylor, R.J.K., Ed., Oxford University Press: Oxford, 1994, ch. 8.
188. (c) Miao, G.; Rossiter, B.E. J. Org. Chem. 1995, 60, 8424.
189. (d) Handke, G.; Krause, N. Tetrahedron Lett. 1993, 34, 6037.
190. Martinelli, M.J.; Peterson, B.C.; Khau, V.V.; Hutchison, D.R.; Leanna, M.R.; Audia, J.E.; Droste, J.J.; Wu, Y.D.; Houk, K.N. J. Org. Chem. 1994, 59, 2204.
191. (a) Ho, T.L. Tandem Organic Reactions; Wiley-Interscience: New York, 1992.
192. (b) Wang, K.K.; Wang, Z.; Tarli, A.; Gannett, P. J. Am. Chem. Soc. 1996, 118, 10783.