Synthesis of nonracemic phosphonates

Tetrahedron

Volumn 53, Issue 49, 1997, Pages 16609-16644

  Wiemer, David F ^a  

^a E11 SSH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IONOPHORE; METAL; PHOSPHONIC ACID DERIVATIVE;

ACYLATION; ALKYLATION; ANTIBODY PRODUCTION; CATALYST; OXIDATION; POLYMERIZATION; PRIORITY JOURNAL; PROTON TRANSPORT; REDUCTION; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030810309     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10305-2     Document Type: Review

References (195)

1. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
2. Engel, R. Chem. Rev. 1977, 77, 349-367.
3. Lerner, R. A; Benkovic, S. J.; Schultz, P. G. Science 1991, 252, 659-667.
4. Seebach, D. Angew. Chem. Int. Ed. Engl. 1990, 29, 1320-1367
5. Almeida, W. P.; Correia, C. R. D. Tetrahedron Lett. 1994, 35, 1367-1370 and references cited therein.
6. Jacks, T. E.; Nibbe , H.; Wiemer, D. F. J. Org Chem. 1993, 58, 4584-4588.
7. Lalinde, N.; Tropp, B. E.; Engle, R. Tetrahedron 1983, 14, 2369-2372.
8. Blackburn, G. M. Chem. Ind. (London) 1981, 134-138.
9. Cooperman, B. S.; Chiu, N. Y. Biochem. 1973, 12, 1670-1676.
10. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587-5590.
11. b) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591-5594.
12. Sikorski, J. A.; Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Corey, S. D.; Font, J. L.; Gruys, K. J.; Han C. Y.; Lin, K. C.; Pansegrau, P. D.; Ream, J. E.; Schnur, D.; Shah, A.; Walker, M. C. Phosphorus, Sulfur, and Silicon 1993, 76, 375-378.
13. Pompliano, D. L.; Rands, E.; Schaber, M. D.; Mosser, S. D.; Anthony, N. J.; Gibbs, J. B. Biochemistry 1992, 37, 3800-3807.
14. Stowasser, B.; Budt, K. H.; Li, J. Q.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625-6628.
15. a) Kafarski, P.; Lejczak, B. Phosphorus, Sulfur, and Silicon 1991, 63, 193-215.
16. b) Smith, A. B., III; Yager, K. M., Taylor, C. M. J. Am. Chem. Soc. 1995, 117, 10879-10888.
17. Shokat, K. M.; Ko, M. K.; Scanlan, T. S.; Kochersperger, L.; Yonkovich, S.; Thaisrivongs, S.; Schultz, P. G. Angew. Chem. Int. Ed. Engl. 1990, 29, 1296-1303.
18. Nakayama, G. R.; Schultz, P. G. J. Am. Chem. Soc. 1992, 114, 780-781.
19. a) Yager, K. M.; Taylor, C. M.; Smith, A. B., III J. Am. Chem. Soc. 1994, 116, 9377-9378.
20. b) Wagner, J.; Lerner, R. A.; Barbas, C. F. III Bioorg. Med. Chem. 1996, 4, 901-916.
21. a) Janda, K. D.; Benkovic, S. J.; Lerner, R. A. Science 1989, 244, 437-439.
22. b) Janda, K. D.; Ashley, J. A; Jones, T. M.; McLeod, D. A.; Schloeder, D. M.; Weinhouse, M. I.; Lerner, R. A.; Gibbs, R. A.; Benkovic, P. A.; Hilhorst, R.; Benkovic, S. J. J. Am. Chem. Soc. 1991, 113, 291-297.
23. Yokomatsu, T.; Yoshida, Y.; Shibuya, S. J. Org. Chem. 1994, 59, 7930-7933.
24. b) Baraldi, P. G.; Guarneri, M.; Moroder, F.; Pollini, G. P.; Simoni, D. Synthesis 1982, 653-655.
25. c) Gouverneur, V.; Lalloz, M-N. Tetrahedron Lett. 1996, 37, 6331-34.
26. d) Benayoud, F.; deMendonca, D. J.; Digits, C. A.; Moniz, G. A.; Sanders, T. C.; Hammond, G. B. Org. Chem. 1996, 61, 5159-5164.
27. e) Öhler, E.; Zbiral, E.; Synthesis 1991, 357-361.
28. f) Öhler, E.; Kanzler, S. Synthesis 1995, 539-543, and references therein.
29. Mjalli, M. M.; Cao, X. Tetrahedron Lett. 1996, 37, 6073-6076.
30. Pudovic, A. N.; Konovalova, I. V. Synthesis 1979, 81-96, and references cited therein.
31. Abramov, V. S.; Dokl. Akad. Nauk. S. S. S. R. 1950, 73, 487-489; Chem. Abstr. 1951, 45, 2855h.
32. Abramov, V. S.; Dokl. Akad. Nauk. S. S. S. R. 1950, 73, 487-489; Chem. Abstr. 1951, 45, 2855h.
33. b) For an early application to steroids, cf: Benezra, C.; Ourisson, G. Bull. Soc. Chim. Fr. 1967, 624-632.
34. Paulsen, H.; Greve, W.; Kuhne, H. Tetrahedron Lett. 1971, 12, 2109-2112.
35. a) Evelyn, L.; Hall, L. D.; Steiner, P. R.; Stokes, D. H. J. Chem. Soc., Chem Commun. 1969, 576-577.
36. b) Evelyn, L.; Hall, L. D.; Lynn, L.; Steiner, P. R.; Stokes, D. H. Carbohydrate Research 1973, 27, 21-27.
37. a) Hammerschmidt, F. Liebigs Ann. Chem. 1991, 469-475.
38. b) The analogous TIPS aldehyde gives even better de: Bongini, A.; Camerini, R.; Panunzio, M.; Tetrahedron: Asymmetry 1996, 7, 1467-1476.
39. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1993, 4, 1401-1404.
40. Serra, C.; Dewynter, G.; Montero, J. L.; Imbach, J. L. Tetrahedron 1994, 50, 8427-8444.
41. a) McEldoon, W. L.; Lee, K.; Wiemer, D. F. Tetrahedron Lett. 1993, 34, 5843-5846.
42. b) McEldoon, W. L.; Wiemer, D. F. Tetrahedron 1995, 51, 7131-7148.
43. Gordon, N. J.; Evans, S. A., Jr. J. Org. Chem. 1993, 58, 5293-5294.
44. a) Blazis, V. J.; Koeller, K. J.; Spilling, C. D. Tetrahedron: Asymmetry 1994, 5, 499-502.
45. b) Blazis, V. J.; Koeller, K. J.; Spilling, C. D. J. Org. Chem. 1995, 60, 931-940.
46. a) Sum, V.; Kee, T. P. J. Chem. Soc., Chem Commun. 1993, 1369-1370.
47. b) Devitt, P. G.; Kee, T. P. J. Chem. Soc. Perkin Trans. I 1994, 3169-3182.
48. c) Sum, V.; Baird, C. A.; Kee, T. P.; Thornton-Pett, M. J. Chem. Soc. Perkin Trans. I 1994, 3183-3200, and references cited therein.
49. Wynberg, H.; Smaardijk, Ab. A. Tetrahedron Lett. 1983, 24, 5899-5900.
50. Smaardijk, Ab. A.; Noorda, S.; van Bolhuis, F.; Wynberg, H.; Tetrahedron Lett. 1985, 26, 493-496.
51. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1993, 4, 1779-1782.
52. Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1993, 4, 1783-1784.
53. Rath, N. P.; Spilling, C. D. Tetrahedron Lett. 1994, 35, 227-230.
54. a) Arai, T.; Bougauchi, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927.
55. b) A binaphthoxide catalyst has also been reported: Sasai, H.; Bougauchi, M.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 2717-2720.
56. Mitchell, M. C.; Cawley, A.; Kee, T. P. Tetrahedron Lett. 1995, 36, 287-290.
57. Creary, X.; Geiger, C. C.; Hilton, K. J. Am. Chem. Soc. 1983, 105, 2851-2858.
58. Gajda, T. Tetrahedron: Asymmetry 1994, 5, 1965-1972.
59. a) Meier, C.; Laux, W. H. G. Tetrahedron 1996, 52, 589-598.
60. b) Meier, C.; Laux, W. H. G.; Bats, J. W. Liebigs Ann. Chem. 1995, 1963-1979.
61. Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611-614.
62. a) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931-2932.
63. b) Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769-5772.
64. β-Keto thiophosphonates undergo a similar reduction with excellent ee's: Gautier, I.; Ratovelomanana-Vidal, V.; Savignac, P.; Genet, J. P. Tetrahedron Lett. 1996, 37, 7721-7724.
65. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H. L.; Morikawa, K.; Wang, Z. -M.; Xu, D.; Zhang, X. -L.; J. Org. Chem. 1992, 57, 2768-2771.
66. a) Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 365-368.
67. b) Lohray, B. B.; Maji, D. K.; Nandanan, E. Indian J. Chem. 1995, 34B, 1023-1025.
68. Hampton, A.; Perini, F.; Harper, P. J. Biochemistry 1973, 12, 1730-1736.
69. A recent study reported that hydroboration/oxidation of vinyl phosphonates is ∼100% regioselective for the α-hydroxy phosphonate: Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1991, 113, 7424-7426.
70. a) Davis, F. A.; Haque, M. S.; Ulatowski, T. G.; Towson, J. C. J. Org. Chem. 1986, 51, 2402-2404.
71. b) Davis, F. A.; Weismiller, M. C.; Murphy, C K.; Thimma Reddy, R.; Chen, B. C. J. Org. Chem. 1992, 57, 7274-7285.
72. Gala, D.; DiBenedetto, D. J.; Mergelsberg, I.; Kugelman, M. Tetrahedron Lett. 1996, 37, 8117-8120.
73. Pogatchnik, D. M.; Wiemer, D. F. Tetrahedron Lett. 1997, 38, 3495-3498.
74. Gulea-Purcarescu, M.; About-Jaudet, E.; Collignon, N.; Tetrahedron Lett. 1995, 36, 6635-6638.
75. Denmark, S. E.; Miller, P. C. Tetrahedron Lett. 1995, 36, 6631-6634.
76. Denmark, S. E.; Chen, C. T. J. Am. Chem. Soc. 1995, 117, 11879-11897.
77. Hammerschmidt, F.; Hanninger, A. Chem. Ber. 1995, 128, 823-830.
78. a) Hammerschmidt, F.; Vollenkle, H. Liebigs Ann. Chem. 1986, 2053-2064.
79. b) (1-Naphthyl)ethylamine was used to resolve 1-hydroxyethylphosphinic acid, which was oxidized to the phosphonic acid: Sasaki, M. Agric. Biol. Chem. 1986, 50, 741-745.
80. Hammerschmidt, F.; Vollenkle, H. Liebigs Ann. Chem. 1989, 577-583.
81. Mori, I.; Iwasaki, G.; Kimura, Y.; Matsunaga, S. I.; Ogawa, A.; Nakano, T.; Buser, H. P.; Hatano, M.; Tada, S.; Hayakawa, K. J. Am. Chem. Soc. 1995, 117, 4411-4412.
82. Li, Y. F.; Hammerschmidt, F. Tetrahedron: Asymmetry 1993, 4, 109-120.
83. Drescher, M.; Li,. Y. F.; Hammerschmidt, F.; Tetrahedron 1995, 51, 4933-4946.
84. Khushi, T.; O'Toole, K. J.; Sime, J. T. Tetrahedron Lett. 1993, 34, 2375-2378.
85. Heisler, A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hagele, G.; Levayer, F. Tetrahedron: Asymmetry 1993, 4, 959-960.
86. a) Li, Z.; Racha, S.; Dan, L. El-Subbagh, H.; Abushanab, E. J. Org. Chem. 1993, 58, 5779-5783.
87. b) Pragnacharyulu, P. V. P.; Abushanab, E. Tetrahedron Lett. 1995, 36, 5507-5510.
88. Page, P.; Blonski, C.; Perie, J. Tetrahedron Lett. 1995, 36, 8027-8031.
89. a) Ackerman, B.; Jordan, T. A.; Eddy, C. R.; Swern, D. J. Am. Chem. Soc. 1956, 78, 4444-4447.
90. b) Berlin, K. D.; Hellwege, D. M.; Nagabhushanam, M. J. Org. Chem. 1965, 30, 1265-1267
91. c) Zhdanov, Y. A.; Uzlova, L. A.; Glebova, Z. I. Russ. Chem. Rev. 1980, 49, 843-853.
92. Karaman, R.; Goldblum, A.; Breuer, E. J. Chem. Soc. Perkin Trans. I 1989, 765-774.
93. Afarinkia, K.; Echenique, J.; Nyburg, S. C. Tetrahedron Lett. 1997, 38, 1663-1666.
94. Oshikawa, T.; Yamashita, M. Bull. Chem. Soc. Jpn. 1990, 63, 2728-2730.
95. a) Longmire, C. F.; Evans, S. A., Jr. J. Chem. Soc. Chem. Commun. 1990, 922-923;
96. b) Telan, L. A.; Poon, C. D.; Evans, S. A., Jr. J. Org. Chem. 1996, 61, 7455-7462.
97. Newer methods of β-keto phosphonate synthesis, not yet been applied to preparation of nonracemic compounds, include: a) Kim, D. Y.; Kong, M. S.; Kim, T. H.; Synth. Commun. 1996, 26, 2487.
98. b) Lee, C. W.; Hong, J. E.; Oh, D. Y. J. Org. Chem. 1995, 60, 7027-7029.
99. c) Kim, D. Y.; Kong, M. S. J. Chem. Soc., Chem. Commun. 1994, 3359-3360.
100. d) Koh, Y. J.; Oh, D. Y. Tetrahedron Lett. 1993, 34, 2147-2148.
101. e) Hong, S.; Chang, K.; Ku, B.; Oh, D. Y. Tetrahedron Lett. 1989, 30, 3307-3308.
102. Arbuzov, B. A Pure Appl. Chem. 1964, 9, 307-335.
103. Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415-430.
104. a) Perkow, W.; Ullerich, K; Meyer, F. Naturwissenschaften 1952, 39, 353.
105. b) Bianchini, J.P.; Gaydou, E. M. C. R. Hebd. Seances Acad. Sci., Ser. C 1975, 280, 1521-1523.
106. c) Baroulare, M.; Sturtz, G. Bull. Soc. Chim. Fr. 1974, 7-8, 1585-1590.
107. d) Gaydou, E.M.; Bianchini, J.P. Chem. Commun. 1975, 14, 541-542.
108. Where the Arbuzov reaction proves difficult, a Michaelis-Arbuzov reaction may be useful: Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K.; Ogawa, Y. J. Am. Chem. Soc. 1988, 110, 4685-4696. Both allylic (Falck, J. R.; Abdali, A.; Wittenberger, S. J. J. Chem. Soc. Chem. Commun. 1990, 953-955) and propargylic (Kerdesky, F. A. J.; Schmidt, S. P.; Brooks, D. W. J. Org. Chem. 1993, 58, 3516-3520) halides have been used to prepare nonracemic phosphonates.
109. Where the Arbuzov reaction proves difficult, a Michaelis-Arbuzov reaction may be useful: Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K.; Ogawa, Y. J. Am. Chem. Soc. 1988, 110, 4685-4696. Both allylic (Falck, J. R.; Abdali, A.; Wittenberger, S. J. J. Chem. Soc. Chem. Commun. 1990, 953-955) and propargylic (Kerdesky, F. A. J.; Schmidt, S. P.; Brooks, D. W. J. Org. Chem. 1993, 58, 3516-3520) halides have been used to prepare nonracemic phosphonates.
110. Where the Arbuzov reaction proves difficult, a Michaelis-Arbuzov reaction may be useful: Nicolaou, K. C.; Daines, R. A.; Chakraborty, T. K.; Ogawa, Y. J. Am. Chem. Soc. 1988, 110, 4685-4696. Both allylic (Falck, J. R.; Abdali, A.; Wittenberger, S. J. J. Chem. Soc. Chem. Commun. 1990, 953-955) and propargylic (Kerdesky, F. A. J.; Schmidt, S. P.; Brooks, D. W. J. Org. Chem. 1993, 58, 3516-3520) halides have been used to prepare nonracemic phosphonates.
111. a) Corey, E. J.; Kwiatkowski, G.T. J. Am. Chem. Soc. 1966, 88, 5654-5656.
112. b) Mathey, F.; Savignac, P. Tetrahedron 1978, 34, 649-654.
113. Aboujaoude, E. E., Collignon, N.; Savignac, P. J. Organomet. Chem. 1984, 264, 9-17.
114. a) Rosen, T.; Heathcock, C. H. J. Am. Chem. Soc. 1985, 107, 3731-3733.
115. b) Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1988, 58, 2374-2378.
116. c) Karanewsky, D. S.; Malley, M. F.; Gougoutas, J. Z. J. Org. Chem. 1991, 56, 3744-3747.
117. Altenbach, H. J.; Holzapfel, W. Angew. Chem. Int. Ed. Engl. 1990, 29, 67-68.
118. Narkunan, K.; Nagarajan, M. J. Org. Chem. 1994, 59, 6386-6390.
119. Koskinen, A. M. P.; Krische, M. J. Synlett 1990, 665-666.
120. Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61 4666-4675.
121. Kojima, K.; Saito, S. Synthesis 1992, 949-950.
122. a) Hanessian, S.; Rancourt, G.; Guidon, Y. Can. J. Chem. 1978, 56, 1843-1846.
123. b) Aristoff, P. A. J. Org. Chem. 1981, 46, 1954-1957.
124. c) Ditrich, K. Hoffmann, R. W. Tetrahedron Lett. 1985, 26, 6325-6328.
125. d) Heathcock, C. H.; von Geldern, T. W. Heterocycles 1987, 25, 75-78.
126. e) Paterson, I.; Laffan, D. D. P.; Rawson, D. J. Tetrahedron Lett. 1988, 29, 1461-1464.
127. f) Yamanoi, T.; Akiyama, T.; Ishida, E.; Abe, H.; Ameniya, M.; Inazu, T. Chem. Lett. 1989, 335-336.
128. g) Harre, M.; Trabandt, J.; Westermann, J. Liebigs Ann. Chem. 1989, 1081-1083.
129. h) Coe, J. W.; Roush, W. R. J. Org. Chem. 1989, 54, 915-930.
130. i) Han, Q.; Wiemer, D. F. J. Am. Chem. Soc. 1992, 114, 7692-7697.
131. j) Delamarche, I.; Mosset, P. J. Org. Chem. 1994, 59, 5453-5457.
132. k) Mulzer, J.; Martin, H. J.; List, B. Tetrahedron Lett. 1996, 37, 9177-9178.
133. l) Knol, J.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 2527-2530.
134. Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1997, 62, 4313-4320.
135. Nicolaou, K. C.; Pavia, M. R.; Seitz, S. P. J. Am. Chem. Soc. 1981, 103, 1224-1226.
136. b) Nicolaou, K. C.; Seitz, S. P.; Pavia, M. R.; Petasis, N. A. J. Org. Chem. 1979, 44, 4011-4013.
137. Paterson, I.; Yeung, K. S. Tetrahedron Lett. 1993, 33, 5347-5350.
138. Lim, M. I.; Marquez, V. E. Tetrahedron Lett. 1983, 24, 4051-4054.
139. Mikolajczyk, M.; Balcewski, P. Synthesis 1984, 691-694.
140. Kabat, M. M. Tetrahedron Lett. 1993, 34, 8543-8544.
141. a) Calogeropoulou, T.; Hammond, G.B.; Wiemer, D.F. J. Org. Chem. 1987, 52, 4185-4190.
142. b) Gloer, K.B.; Calogeropoulou, T.; Jackson, J.A.; Wiemer, D.F. J. Org. Chem. 1990, 55, 2842-2846.
143. c) An, Y. Z.; Wiemer, D.F. J. Org. Chem. 1992, 57, 317-321.
144. d) Koerwitz, F. L.; Hammond, G. B.; Wiemer, D.F. J. Org. Chem. 1989, 54, 738-743.
145. Clarke, R. Gahagan, M.; Mackie, R. K.; Foster, D. F.; Cole-Hamilton, D. J.; Nicol, M.; Montford, A. W. J. Chem. Soc. Dalton Trans. I 1995, 1221-1226.
146. a) Jackson, J.A.; Hammond, G.B.; Wiemer, D.F. J. Org. Chem. 1989, 54, 4750-4754.
147. b) Lee, K.; Jackson, J. A.; Wiemer, D. F. J. Org. Chem. 1993, 58, 5967-5971.
148. a) An, Y. Z.; An, J. G.; Wiemer, D. F. J. Org. Chem. 1994, 59, 8197-8202.
149. b) An, J.; Wilson, J. M.; An, Y. Z.; Wiemer, D. F. J. Org. Chem. 1996, 61, 4040-4045.
150. An, J. G.; Wiemer, D. F. J. Org. Chem. 1996, 61, 8775-8779.
151. Lee, K.; Wiemer, D. F. J. Org. Chem. 1991, 56, 5556-5560.
152. Grieco, P. A.; Pogonowski, C. S. J. Am. Chem. Soc. 1973, 95, 3071-3072.
153. Patterson, I.; Boddy, I. Tetrahedron Lett. 1988, 29, 5301-5304.
154. Baccolini, G.; Todesco, P. E.; Dalpozzo, R.; De Nino, A. Gazz. Chim. Ital. 1996, 126, 271-273.
155. Ando, K. J. Org. Chem. 1997, 62, 1934-1939.
156. Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
157. Enders, D.; Wahl, H.; Papadopoulos, K. Liebigs Ann. 1995, 1177-1184.
158. a) Ojea, V.; Fernandez, M. C.; Ruiz, M.; Quintela, J. M. Tetrahedron Lett. 1996, 37, 5801-5804.
159. b) Ojea, V.; Ruiz, M.; Shapiro, G.; Pombo-Villar, E. Tetrahedron Lett. 1996, 35, 3273-3276.
160. Rein, T.; Reiser, O. Acta Chem. Scand. 1996, 50, 369-379.
161. Tomoskozi, I.; Janzso, G. Chem. Ind (London) 1962, 2085-2086.
162. Hatakeyama, S.; Sataoh, K.; Sakurai, K.; Takano, S. Tetrahedron Lett. 1987, 28, 2713-2716
163. b) Hatakeyama, S.; Sataoh, K.; Sakurai, K.; Takano, S. Tetrahedron Lett. 1987, 28, 2717-2720.
164. a) Burri, K. F.; Cardone, R. A.; Chen, W. Y.; Rosen, P. J. Am. Chem. Soc. 1978, 100, 7069-7071.
165. b) Stork, G.; Nakamura, E. J. Org. Chem. 1979, 44, 4010-4011.
166. c) Oppolzer, W.; Dupuis, D.; Poli, G.; Raynham, T. M.; Bernardinelli, G. Tetrahedron Lett. 1988, 29, 5885-5888.
167. d) Franck-Neumann, M.; Briswalter, C.; Chemla, P.; Martina, D. Synlett. 1990, 637-6640.
168. e) Abiko, A.; Masamune, S. Tetrahedron Lett. 1996, 37, 1077-1080.
169. a) Meyers, A. I.; Roland, D. M.; Comins, D. L.; Henning, R.; Fleming, M. P.; Shimizu, K. J. Am. Chem. Soc. 1979, 101, 4732-4734.
170. b) Meyers, A. I.; Comins, D. L.; Roland, D. M.; Henning, R.; Shimizu, K. J. Am. Chem. Soc. 1979, 101, 7104-7105.
171. Keck, G. E.; Boden, E. P.; Wiley, M. R. J. Org. Chem. 1989, 54, 896-906.
172. Tanaka, K.; Ohta, Y.; Fuji, K. Tetrahedron Lett. 1993, 34, 4071-4074.
173. Narasaka, K.; Hidai, E.; Hayashi, Y.; Gras, J. L. J. Chem. Soc., Chem Commun. 1993, 102-104.
174. Denmark, S. E.; Rivera, I. J. Org. Chem. 1994, 59, 6887-6889.
175. Mandai, T.; Kaihara, Y.; Tsuji, J. J. Org. Chem. 1994, 59, 5847-5849.
176. Boeckman, R. K., Jr.; Kamenecka, T. M.; Nelson, S. G.; Pruitt, J. R.; Barta, T. E. Tetrahedron Lett. 1991, 32, 2581-2584.
177. Lee, K.; Wiemer, D. F.; Phosphorus, Sulfur, and Silicon 1993, 75, 87-90.
178. Commins, D. L.; Jacobine, A. F.; Marshall, J. L.; Turnbull, M. M. Synthesis 1978, 309-311.
179. Paquette, L. A.; Wang, T. Z.; Phillippo, C. M. G.; Wang, S. J. Am. Chem. Soc. 1994, 116, 3367-3374.
180. Tanaka, K.; Ohta, Y.; Fuji, K. J. Org. Chem. 1995, 60, 8036-8043.
181. Hua, D. H.; Chan-Yu-King, R.; McKie, J. A.; Myer, L. J. Am. Chem. Soc. 1987, 109, 5026-5029.
182. Denmark, S. E.; Kim, J. H. J. Org. Chem. 1995, 60, 7535-7547.
183. Hanessian, S.; Gomtsyan, A.; Payne, A.; Herve, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034.
184. a) Boyle, C. D.; Kishi, Y. Tetrahedron Lett. 1995, 36, 4579-4582.
185. b) Wang, T. Z.; Pinard, E.; Paquette, L. A. J. Am. Chem. Soc. 1995, 118, 1309-1318.
186. a) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393-10394;
187. b) Hanessian, S.; Cantin, L. D.; Roy, S.; Andreotti, D.; Gomtsyan, A. Tetrahedron Lett. 1997, 38, 1103-1106.
188. Callot, H. J.; Benezra, C. Can. J. Chem. 1970, 48, 3382.
189. Peterson, A. C.; Levsen, S. M.; Cremer, S. E. Phosphorus, Sulfur, and Silicon 1996, 115, 241-254.
190. Barton, D. H. R.; Gero, S. D.; Quiclet-Sire, B.; Samadi, M. Tetrahedron 1992, 48, 1627-1636.
191. Wnuk, S.; Robins, M. J. J. Am. Chem. Soc. 1996, 118, 2519-2520.
192. Holt, D. A.; Erb, J. M. Tetrahedron Lett. 1989, 30, 5393-5396.
193. Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630-4632.
194. Vedejs, E.; Garcia-Rivas, J. A. J. Org. Chem. 1994, 59, 6517-6518.
195. Burke, S. D.; O'Donnell, C. J.; Hans, J. J.; Moon, C. W.; Ng, R. A.; Adkins, T. W.; Packard, G. K. Tetrahedron Lett. 1997, 38, 2593-2596.