Recent developments in the synthesis and utilization of chiral sulfoxides

Chemical Reviews

Volumn 103, Issue 9, 2003, Pages 3651-3705

  Fernández, Inmaculada ^a,b   Khiar, Noureddine ^a,b  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^b UNIVERSITY OF SEVILLE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHEMICAL BONDS; DERIVATIVES; HYDROGENATION; HYDROLYSIS; OXIDATION; STEREOCHEMISTRY; STRUCTURE (COMPOSITION); SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TITANIUM;

BENZALDEHYDE; CATALYTIC CYCLOADDITION; CATALYTIC HYDROGENATION; CHIRAL OXAZIRIDINE; CHIRAL PEROXIDE; CHIRAL SULFOXIDE; DIASTEREOSELECTIVE SULFOXIDATION; ENANTIOSELECTIVE BIOLOGICAL SULFOXIDATION; METAL-SULFOXIDE BONDING; NUCLEOPHILIC SUBSTITUTION;

SULFUR COMPOUNDS;

EID: 0141508049     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr990372u     Document Type: Article

References (391)

1. (a) Mislow, K.; Simmons, T.; Melillo, J. T.; Ternay, A. L. J. Am. Chem. Soc. 1964, 86, 14952.
2. (b) Mislow, K.; Green, H. M.; Laur, P.; Melillo, J. T.; Simmons, T.; Ternay, A. L. J. Am. Chem. Soc. 1965, 87, 1958.
3. Solladié, G. Synthesis 1981, 185.
4. (a) Rayner, D. R.; Gordon, A. J.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4854.
5. (b) Mislow, K.; Siegel, J. J. Am. Chem. Soc. 1984, 106, 3319.
6. (a) Solladié, G.; Greck, C.; Demailly, G.; Solladié-Cavallo, A. Tetrahedron Lett. 1982, 5047.
7. (b) Kosugi, H.; Konta, H.; Uda, H. J. Chem. Soc., Chem. Commun. 1985, 211.
8. (c) Carreño, M. C.; Garcia-Ruano, J. L.; Martin, A. M.; Pedregal, C.; Rodríguez, J.; Rubio, A.; Sánchez, G.; Solladié, G. J. Org. Chem. 1990, 55, 2120.
9. Solladié, G.; Collobert, F.; Sonny, F. Tetrahedron Lett. 1999, 40, 1227.
10. Andersen, K. K. In The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappaport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons: New York, 1988; Chapter 3, p 56.
11. Solladié, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, Chapter 3, p 148.
12. Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961.
13. Khiar, N.; Fernández, I.; Alcudia, A.; Alcudia, F. In Advances in Sulfur Chemistry 2; Rayner, C. M. Ed.; JAI Press Inc.: Stamford, CT, 2000; Chapter 3, p. 57.
14. A review series dealing with the synthesis of sulfur and selenol derivatives in general, begun in 1994, contains a section on enantio- and diastereoselective synthesis of sulfoxides: (a) Rayner, C. M. Contemp. Org. Synth. 1994, 1, 191.
15. (b) Procter, D. J. Chem. Soc., Perkin Trans. 2001, 335 and references therein.
16. (a) Posner, G. H. Acc. Chem. Res. 1987, 20, 72.
17. (b) Posner, G. H. In The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappaport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons: New York, 1988; Chapter 16, p 823.
18. Solladié, G. In Asymmetric Synthesis; Morrison J. D., Ed.; Academic Press: New York, 1983; Vol. 2, p 157.
19. (a) Hua, D. H. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press: London, 1992; Vol. 1, p 249.
20. (b) Hua, D. H. Adv. Heterocycl. Nat. Prod. Synth. 1996, 3, 151.
21. Solladié, G.; Carreño, M. C. In Organosulphur Chemistry. Synthetic Aspects; Page, P. C. B., Ed.; Academic Press: New York, 1995; Chapter 1, p. 1.
22. Arai, Y.; Koizumi, T. Sulfur Rep. 1993, 15, 41.
23. Lee, A. W. M.; Chan, W. H. Top. Curr. Chem. 1997, 190, 103.
24. Garcia Ruano, J. L.; Carretero, J. C.; Carreño, M. C.; Martín, L. C.; Urbano, A. Pure Appl. Chem. 1996, 68, 925.
25. Garcia Ruano, J. L.; Cid, B. Top. Curr. Chem. 1999, 204, 1.
26. (a) Renaud, P., Gerster, M. Angew. Chem., Int. Ed. 1998, 37, 2562.
27. (b) Renaud, P. Chimia 1997, 51, 236.
28. Toru, T.; Watanabe, Y.; Mase, N.; Tsusaka, M.; Hayakawa, T.; Ueno, Y. Pure Appl. Chem. 1996, 68, 711.
29. Carrenõo, M. C. Chem. Rev. 1995, 95, 1717.
30. Matsuyama, H. Sulfur Rep. 1999, 25, 85.
31. Kjaer, A. Pure Appl. Chem. 1977, 49, 137.
32. Tomaszewski, J.; Rumore, M. M. Drug. Dev. Ind. Pharm. 1994, 20, 119.
33. (a) An exception is the following article on the development of esomeprazole that appeared after the submission of this review: Carlsson, E.; Lindberg, P.; von Unge, S. Chem. Br. 2002, May 42.
34. (b) Lindberg, P.; Bränstrom, A.; Wallmark, B.; Mattson, H.; Rikner, L.; Hoffman, K.-J. Med. Res. Rev. 1990, 10, 1.
35. Werhling, A. W.; Weidmann, K. In Burger's Medicinal Chemistry and Drug Discovery; Wolff, M., Ed.; John Wiley & Sons: New York, 1996; Vol. 2, Chapter 27, p 119.
36. Renfrey, S.; Featherstone, J. Nature Rev. Drug. Discov. 2002, 1, 175.
37. (a) Kubec, R.; Svobodova, M.; Velisek, J. J. Agric. Food Chem. 2000, 48, 428.
38. (b) Komatsu, W.; Miura, Y.; Yagasaki, K. Lipids 1998, 33, 499.
39. (c) Kyung, K. H.; Han, D. C.; Fleming, H. P. J. Food. Sci. 1997, 62, 406.
40. Okamoto, K.; Nishito, T. J. Biol. Chem. 1995, 270, 7816.
41. Ashton, M.J.; Bridge, A.W.; Bush, R.C.; Dron, D.I.; Harris, N.V.; Jones, G.D.; Lythgoe, D.J.; Ridell, D.; Smith C. Bioorg. Med. Chem. Lett. 1992, 2, 375.
42. Brown, T.J.; Chapman, R.F.; Cook, D.C.; Hart, T.W.; McLay, I.M.; Jordan, R.; Mason, J.S.; Palfreyman, M.N.; Walsh, R.J.A.; Withnall, M.T.; Aloup, J.-C.; Cavero, I.; Fargen D.; James, C.; Mondot, S. J. Med. Chem. 1992, 35, 3613.
43. Ortega, M.P.; Garcia, M.D.C.; Gijon, M.A.; Casa-Juana, M.F.D.; Priego, J.G.; Crespo, M.S.; Sunkel, C. J. Pharmacol. Exp. Ther. 1990, 255, 28.
44. Zhang, Y.; Talay, P.; Cho, C.-G.; Posner, G.H. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2399.
45. Parry, R.J.; Li, Y; Gomez, E.E. J. Am. Chem. Soc. 1992, 114, 5946.
46. Farrell, N.; Kiley, D.M.; Schmidt, W.; Hacker, M.P. Inorg. Chem. 1990, 29, 397.
47. Chooi, S.Y.M.; Leung, P.H.; Sim, K.Y.; Tan, K.S.; Kon, O.L. Tetrahedron: Asymmetry 1994, 5, 49.
48. Fox, A.E.; Gawlak, D.L.; Ballantyne, D.L., Jr.; Freedman, H.H. Transplantation 1973, 15, 389.
49. Uno, T.; Ozaki, Y.; Koga, Chu, G.; Okada, M.; Tamura, K.; Igawa, F.; Umeki, F.; Kido, M.; Nishi, T. Chem. Pharm. Bull. 1995, 43, 1824.
50. Hoveyda, A.H.; Evans, D.A.; Fu, G. Chem. Rev. 1993, 93, 1307.
51. (a) Shimazaki, M.; Takahashi, M.; Komatsu, H.; Ohta, A.; Kaji, K.; Kadoma, Y. Synthesis 1992, 555.
52. (b) Shimazaki, M.; Komatsu, H.; Ohta, A.; Kadoma, Y. Synthesis 1992, 957.
53. De Lucchi, O., Lucchini, V.; Marchioro, C.; Valle, G.; Modena, G. J. Org. Chem. 1986, 51, 1457.
54. De Lucchi, O. Bull. Soc. Chim. Belg. 1988, 97, 679.
55. Breithschuh, R; Seebach, D. Synthesis 1992, 555.
56. Annunziata, R.; Cinquini, M.; Cozzi, F.; Farina, S.; Montanari, V. Tetrahedron 1987, 43, 1013.
57. Escher, B.M.; Haynes, R.K.; Kremmydas, S.; Ridley, D.D. J. Chem. Soc., Chem. Commun. 1988, 137.
58. Khiar, N.; Alonso, I.; Rodríguez, N.; Fernández-Mayoralas, A.; Jiménez-Barbero, J.; Nieto, O.; Cano, F.; Foces-Foces, C.; Martín-Lomas, M. Tetrahedron Lett. 1997, 38, 8267.
59. Khiar, N. Tetrahedron Lett. 2000, 41, 9059.
60. Crich, D.; Mataka, J., Sun, S.; Lam, K.-C.; Rheingold, A.L.; Wink, D. Chem. Commun. 1998, 2763.
61. Davis, M.; Wu, W.-Y. Aust. J. Chem. 1986, 39, 1165.
62. Danelon, G.O.; Mata, E.G.; Mascaretti, O.A. Tetrahedron Lett. 1993, 34, 7877.
63. Glass, R.S.; Liu, Y. Tetrahedron Lett. 1994, 23, 3887.
64. Sato, T.; Otera, J. Synlett 1995, 365.
65. Bower, E.F.; Williams, J.M.J. Tetrahedron Lett. 1994, 45, 7111.
66. Bower, E.F.; Martin, C.J.; Rawson, D.J.; Slawin, A.M.Z.; Williams, J.M.J. J. Chem. Soc., Perkin Trans. 1 1995, 333.
67. Poss, K.M.; Chao, S.T.; Gordon, E.M.; McCann, P.J.; Santafianos, D.P.; Traeger, S.C.; Varma, R.K.; Washburn, W.N. Tetrahedron. Lett. 1994, 21, 3461.
68. Nkajima, N.; Enomoto, T.; Matsuura, N.; Ubukata, M. Bioorg. Med. Chem. Lett. 1998, 8, 3331.
69. Porse, B.T.; Kirillow, S.V.; Awayez, M.J.; Ottenheijm, H.C.J.; Garrett, R.A. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 9003.
70. Ubukata, M.; Morita, T.; Uramoto, M., Osada, H. J. Antibiot. 1996, 49, 1096.
71. Holland, H.L, Chem. Rev. 1988, 88, 473.
72. Holland, H.L. Organic Synthesis with Oxidative Enzymes; VCH: New York, 1992; p 255.
73. Colonna, S. In Stereocontrolled Organic Synthesis; Trost, B., Ed.; Blackwell: London, 1994; p 435.
74. Mata, E.G. Phosphorus Sulfur 1996, 117, 231.
75. Holland, H.L. Nat. Prod. Rep. 2001, 18, 171.
76. Light, D.R.; Waxman, D.J.; Walsh, C.T. Biochemistry 1982, 21, 2490.
77. Carrea, G.; Redigolo, B.; Riva, S.; Colonna, S.; Gaggero, N.; Battistel, E.; Bianchi, D. Tetrahedron: Asymmetry 1992, 3, 1063.
78. Ottolina, G.; Pasta, P.; Carrea, G.; Colonna, S.; Dallavalle, S.; Holland, H.L. Tetrahedron: Asymmetry 1995, 6, 1375.
79. Colonna, S.; Gaggero, N.; Manfredi, A.; Casella, L.; Gullotti, M. J. Chem. Soc., Chem. Commun. 1995, 1123.
80. Colonna, S.; Gaggero, N.; Pasta, P.; Ottolina, G. J. Chem. Soc., Chem. Commun. 1996, 2303.
81. Shaw, P.D.; Hager, L.P. J. Biol. Chem. 1961, 236, 1626.
82. Kobayashi, S.; Nakaro, M.; Kimura, T.; Schaap, A.P. Biochemistry 1987, 26, 5019.
83. Colonna, S.; Gaggero, N.; Casella, L.; Carrea, G.; Pasta, P. Tetrahedron: Asymmetry 1992, 3, 95.
84. Colonna, S.; Gaggero, N.; Manfredi, A.; Casella, L.; Gullotti, M.; Carrea, G.; Pasta, P. Biochemistry 1990, 29, 10465.
85. van Deurzen, M.P.J.; van Rantwijk, F.; Sheldon, R.A. Tetrahedron 1997, 53, 13183.
86. Fu, H.; Kondo, H.; Ichikawa, Y.; Look, G.C.; Wong, C.H. J. Org. Chem. 1992, 57, 7265.
87. Andersson, M.; Willetts, A.; Allenmark, S. J. Org. Chem. 1997, 62, 8544.
88. Ozaki, S.; Ortiz de Montellano, P.R. J. Am. Chem. Soc. 1995, 117, 7056.
89. Galzigna, L.; Rizzoli, V.; Schiappelli, M.P.; Rigobello, M.P.; Scarpa, M.; Rigo, A. Free Radical Biol. Med. 1996, 20, 807.
90. Miller, V.P.; DePillis, G.D.; Ferrer, J.C.; Mauk, A.G.; Ortiz de Montellano, P.R. J. Biol. Chem. 1992, 267, 8936
91. Colonna, S.; Gaggero, N.; Carrea, G.; Pasta, P. Tetrahedron Lett. 1994, 35, 9103.
92. Colonna, S.; Gaggero, N.; Richelmi, C.; Carrea, G.; Pasta, P. Gazz. Chim. Ital. 1995, 125, 479.
93. Lee, K.; Brand, J.M.; Gibson, D.T. Biochem. Biophys. Res. Commun. 1995, 212, 9.
94. Ozaki, S.; Ortiz de Montellano, P.-R. J. Am. Chem. Soc. 1994, 116, 4487.
95. Ozaki, S.; Ortiz de Montellano, P.-R. J. Am. Chem. Soc. 1995, 117, 7056.
96. Ozaki, S.; Matsui, T.; Watanabe, Y. J. Am. Chem. Soc. 1996, 118, 9784.
97. Ozaki, S.; Matsui, T.; Watanabe, Y. J. Am. Chem. Soc. 1997, 119, 6666.
98. Yamazaki, Y.; Hesse, C.; Okuno, H.; Abraham, W.-R. Appl. Microbiol. Biotechnol. 1996, 45, 595.
99. Cashman, J.R.; Olsen, L.D.; Boyd, D.R.; McMordie, R.A.S.; Dulop, R.; Dalton, H. J. Am. Chem. Soc. 1992, 114, 8772.
100. Boyd, D.R.; Sharma, N.D.; Haughley, S.A.; Kennedy, M.A.; McMurray, B.T.; Sheldrake, G.N.; Allen, C.C.R.; Dalton, H.; Sproule, K. J. Chem. Soc., Perkin Trans. 1 1998, 1929.
101. Holland, H.L.; Brown, F.M.; Laksmaiah, G.; Larsen, B.G.; Patel, M. Tetrahedron: Asymmetry 1997, 8, 683.
102. Holland, H.L.; Brown, F.M.; Larsen, B.G. Tetrahedron: Asymmetry 1994, 5, 1129.
103. Holland, H.L.; Rand, C.G.; Viski, P.; Brown, F.M. Can. J. Chem. 1991, 69, 1989.
104. Madesclaire, M.; Fauve, A.; Metin, J.; Carpy, A. Tetrahedron: Asymmetry 1990, 1, 311.
105. Holland, H.L.; Brown, F.M.; Larsen, B.G. Tetrahedron: Asymmetry 1995, 6, 1561.
106. Buist, P. H.; Marecak, D. M. J. Am. Chem. Soc. 1992, 114, 5073.
107. Beecher, J.; Brackenridge, I.; Roberts, S. M.; Tang, J.; Willetts, A. J. J. Chem. Soc., Perkin Trans. 1 1995, 1641.
108. Tang, I.; Brackenridge, I.; Roberts, S.M.; Beecher, J.; Willetts, A.J. Tetrahedron 1995, 51, 13217.
109. Allen, C.C.R.; Boyd, D.R.; Dalton, H.; Sharma, N.D.; Haughley, S.A.; McMordie, R.A.S.; McMurray, B.T.; Sheldrake, G.N.; Sproule, K. J. Chem. Soc., Chem. Commun. 1995, 119.
110. Fahey, J.W.; Haristoy, X.; Dolan, P.M.; Kensler, T.W.; Sholters, I.; Stephenson, K.K.; Talay, P.; Lozniewski, A. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 7610.
111. Holland, H.L.; Brown, F.M.; Larsen, B.; Zabic, M. Tetrahedron: Asymmetry 1995, 6, 1569.
112. Holland, H.; Brown, F.M. Tetrahedron: Asymmetry 1998, 9, 535.
113. Holland, H.; Andreana, P.R.; Brown, F.M. Tetrahedron: Asymmetry 1999, 10, 2833.
114. Holt, T.; Lindberg, P.; Reeve, C.; Taylor, S. U.S. Patent 5,840,532, 1998.
115. Schultz, P.G.; Lerner, R.A. Science 1995, 269, 1835.
116. Hsieh, L.C.; Stephans, J.C.; Schultz, P.G. J. Am. Chem. Soc. 1994, 116, 2167.
117. Nimri, S.; Keinan, E. J. Am. Chem. Soc. 1999, 121, 8978.
118. Groves, J.T.; Han, Y.; Engen, D.V. J. Chem. Soc., Chem. Commun. 1990, 436.
119. Kagan, H.B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed; VCH: New York 1993; p 203.
120. Kagan, H.B.; Rebiere, F. Synlett 1990, 643.
121. Kagan, H.B.; Luukaas, T. In Transition Metals for Organic Synthesis; Bolm, C., Beller, Eds.: Wiley/VCH: Weinheim, 1999; Vol. 2, p 361.
122. Bolm, C.; Muñiz, K.; Hildebrand, J.P. In Comprehensive Asymmetric Catalysis; Jacobsen, E.N., Pfaltz, A., Yamammoto, H., Eds.; Springer, Berlin, 1999; p 697.
123. Johnson, R.A.; Sharpless, K.B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 227.
124. Pitchen, P.; Kagan, H.B. Tetrahedron Lett. 1984, 24, 1049.
125. Pitchen, P.; Deshmukh, M.N.; Duñach, E.; Kagan, H.B. J. Am. Chem. Soc. 1984, 106, 8188.
126. Kagan, H.B.; Duñach, E.; Nemecek, C.; Pitchen, P.; Samuel, O.; Zhao, S.H. Pure Appl. Chem. 1985, 57, 1911.
127. Duñach, E.; Kagan, H.B. New J. Chem. 1985, 9, 1.
128. Kagan, H.B.; Diter, P. Organosulfur Chem. 1998, 2, 139.
129. (a) Zhao, S.H.; Samuel, O.; Kagan, H.B. Tetrahedron 1987, 43, 5135.
130. (b) Zhao, S.H.; Samuel, O.; Kagan, H.B. Org. Synth. 1989, 68, 49.
131. Brunel, J.M.; Kagan, H.B. Bull. Soc. Chim. Fr. 1996, 133, 1109
132. Brunel, J.M.; Kagan, H.B. Synlett 1996, 404.
133. Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325.
134. Bortolini, O.; Di Furia, F.; Licini, G.; Modena G.; Rossi, M. Tetrahedron Lett. 1986, 27, 6257.
135. Bortolini, O.; Di Furia, F.; Licini, G.; Modena, G. Rev. Heteroat. Chem. 1988, 1, 66.
136. Pitchen, P. In Chirality in Industry II; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; John Wiley & Sons: New York, 1997; p 381.
137. Pitchen, P.; France, C. J.; McFarlane, I. M.; Newton, C. G.; Thompson, D. M. Tetrahedron Lett. 1994, 35, 485.
138. Hart, T. W.; Guillochon, D.; Perrier, G.; Sharp, B. W.; Vacher, B. Tetrahedron Lett. 1992, 33, 5117.
139. Fellenius, E.; Berglinch, T.; Sachs, G.; Olbe, L.; Elander, B.; Sjöstrand, S.-E.; Wallmark, B. Nature 1981, 290, 159.
140. (a) Kohl, B.; Senn-Bilfinger, J. German Patent Appl. DE 403545, priority date November 85, 1990.
141. (b) Lindberg, P.; von Unge, S. Int. Patent Appl. WO 94/27988, priority date May 28, 1993
142. Deng, J.; Chi, Y.; Fu, F.; Cui, X.; Yu, K.; Zhu, J.; Jiang, Y. Tetrahedron: Asymmetry 2000, 11, 1729.
143. von Unge, S.; Langer, V.; Sjölin, L. Tetrahedron: Asymmetry 1997, 8, 1967.
144. Cotton, H.; Elebring, T.; Larsson, M.; Li, L.; Sörensen, H.; von Unge, S. Tetrahedron: Asymmetry 2000, 11, 3819.
145. Davis, F. A.; Kern, J. R.; Kurtz, L. J.; Pfister, J. R. J. Am. Chem. Soc. 1988, 110, 7873.
146. Sunkel, C. E.; Casa-Juana, M. F. D.; Cillero, F. J.; Priego, J. G.; Ortega, M. P. J. Med. Chem. 1988, 31, 1886.
147. Miyashita, K.; Nishimota, M.; Ishino, T.; Murafujii, H.; Obika, S.; Muraoka, O.; Imanishi, T. Tetrahedron 1997, 53, 4279.
148. Okamoto, K.; Nishito, T. J. Biol. Chem. 1995, 270, 7816.
149. Nishi, T.; Uno, T.; Shu, Y.; Tamura, K.; Okada, M. Japan Patent 7-33765, 1995
150. Chem. Abstr. 1995, 122, 160640z.
151. Matsugi, M.; Hashimoto, K.; Inai, M.; Fukuda, N.; Furuta, T.; Minamikawa, J.; Otsuka, S. Tetrahedron: Asymmetry 1995, 6, 2991.
152. Samuel, O.; Ronan, B.; Jagan, H. B. J. Organomet. Chem. 1989, 370, 43.
153. (a) Page, P. C. B.; Namwindwa, E. S.; Klair, S. S.,; Westwood, D. Synlett 1990, 457.
154. (b) Page, P. C. B.; Namwindwa, E. S. Synlett 1991, 80.
155. (c) Page, P. C. B.; Wilkes, R. D.; Barkley, J. V.,; Witty, M. J. Synlett 1994, 547.
156. (d) Page, P. C. B.; Wilkes, R. D.; Witty, M. J. Org. Prep. Proced. Int. 1994, 26, 702.
157. (e) Page, P. C. B.; Wilkes, R. D.; Namwindwa, E. S.; Witty, M. J. Tetrahedron 1996, 52, 2125.
158. (a) Aggarwal, V. K.; Evans, G.; Moya, E., Dowden, J. J. Org. Chem. 1992, 57, 6390.
159. (b) Aggarwal, V. K.; Esquivel-Zamora, B. N.; Evans, G. R.; Jones, E. J. Org. Chem. 1998, 63, 7306.
160. Griffiths, S. L.; Perrio, S.; Thomas, S. E. Tetrahedron: Asymmetry 1994, 5, 545.
161. Diter, P.; Samuel. O.; Taudien, S.; Kagan, H. B. Tetrahedron: Asymmetry 1994, 5, 549.
162. Komatsu, N.; Nishibayashi, Y.; Sugita, T.; Uemura, S. Tetrahedron Lett. 1992, 33, 5391.
163. Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529.
164. Superchi, M. I.; Rosini, C. Tetrahedron: Asymmetry, 1997, 8, 349.
165. Donnoli, M. I.; Superchi, M. I.; Rosini, C. J. Org. Chem. 1998, 63, 9392.
166. Superchi, M. I.; Donnoli, M. I.; Rosini, C. Tetrahedron Lett. 1998, 39, 8541.
167. Yamanoi, Y.; Imamoto, T. J. Org. Chem. 1997, 62, 8560.
168. Takeda, T.; Imamoto, T. Tetrahedron: Asymmetry, 1999, 10, 3209.
169. Reetz, M. T.; Merck, C.; Naberfeld, G.; Rudolph, J. Griebenow, N.; Goddard, R. Tetrahedron Lett. 1997, 38, 5273.
170. Bolm, C.; Dabard, O. A. G. Synlett 1999, 360.
171. Martyn, L. J. P.; Pandaraju, S.; Yudin, A. K. J. Organomet. Chem. 2000, 98, 603.
172. Di Furia, F.; Licini, G.; Modena, G.; Motterle, R.; Nugent, W. J. Org. Chem. 1996, 61, 5175.
173. Bonchio, M.; Licini, G.; Modena, G.,; Bartolini, O.; Moro, S.; Nugent, W. J. Am. Chem. Soc. 1999, 121, 6258.
174. Bonchio, M.; Calloi, S.; DiFuria, F.; Licini, G.; Modena, G.; Moro, S.; Nugent, W. J. Am. Chem. Soc. 1997, 119, 6935.
175. Bonchio, M.; Licini, G.; Di Furia, F.; Mantovani, S.; Modena G.; Nugent, W. J. Org. Chem. 1999, 64, 1326.
176. Colombo, A.; Marturano, G.; Pasini, A. Gazz. Chim. Ital. 1986, 116, 35.
177. (a) Nakajima, K.; Kojima, M.; Fujita, J. Chem. Lett. 1986, 1483.
178. (b) Nakajima, K.; Sasaki, C.; Kojima, M.; Aoyama, T.; Ohba, S.; Sayto, Y.; Fujita, J. Chem. Lett. 1987, 2189.
179. (c) Sasaki, C.; Nakajima, K.; Kojima, M.; Fujita, J. Bull. Chem. Soc. Jpn. 1991, 64, 1318.
180. Palucki, M.; Hanson, P.; Jacobsen, E. N. Tetrahedron Lett. 1992, 33, 7111.
181. Noda, K.; Hosoya, N.; Irie, R.; Yamashita, Y.; Katsuki, T. Tetrahedron 1994, 50, 9609.
182. Noda, K.; Hosoya, N.; Yanai, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1994, 35, 1887.
183. Sasaki, H.; Irie, T.; Ito, Y.; Katsuki, T. Synlett 1994, 356.
184. Kokubo, C.; Katsuki, T. Tetrahedron 1997, 52, 13895.
185. Nakajima, K.; Kojima, M.; Fujita, J. Chem. Lett. 1986, 1483.
186. Bolm, C.; Bienewald, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 2640.
187. Bolm, C.; Bieneweld, F. Synlett 1998, 1327.
188. Vetter, A. H.; Berkessel, A. Tetrahedron Lett. 1998, 39, 1741.
189. Skarewski, J.; Ostrycharz, E.; Siedlecka, R. Tetrahedron: Asymmetry 1999, 10, 3457.
190. Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913.
191. Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919.
192. Davis, F. A.; Sheppard, A. C. Tetrahedron 1988, 45, 5703.
193. Davis, F. A.; Reddy, R. T.; Weismiller, M. C. J. Am. Chem. Soc. 1989, 111, 5964.
194. Davis, F. A.; Towson, J. C.; Weismiller, M. C.; Lal, S.; Carroll, P. J. J. Am. Chem. Soc. 1988, 110, 8477.
195. Davis, F. A.; Weismiller, M. C.; Murphy, C. M.; Reddy, R. T.; Chen, B. C. J. Org. Chem. 1992, 57, 7274.
196. Davis, F. A.; Reddy, R. T.; Han, W.; Carroll, P. J. J. Am. Chem. Soc. 1992, 114, 1428.
197. Rossi, C.; Faure, A.; Madasclaire, M.; Roche, D.; Davis, F. A.; Reddy, R. T. Tetrahedron: Asymmetry 1992, 3, 629.
198. Bethel, D.; Page, P. B.; Vahedi, H. J. Org. Chem. 2000, 65, 6756.
199. Hamann, H. J.; Höft, E.; Mostowicz, D.; Mishnev, A.; Urbanczyk-Lipkoswska, Z.; Chmielewski, M. Tetrahedron 1997, 53, 185.
200. (a) Adam, W.; Hoch, U.; Lazarus, M.; Saha-Moller, C. R.; Schreier, P. J. Am. Chem. Soc. 1995, 117, 11898.
201. Adam, W.; Korb, M. N. Tetrahedron: Asymmetry 1997, 8, 1131.
202. Adam, W.; Korb, M. N.; Roschmann, K. J.; Saha-Moller, C. R. J. Org. Chem. 1998, 63, 3423.
203. Schenk, W. A.; Frisch, J.; Adam, W.; Prechtl, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1609.
204. Schenk, W. A.; Frisch, J.; Dürr, M.; Burzlaf, N.; Stalke, D.; Fleischer, R.; Adam, W.; Prechtl, F.; Smerz, A. K. Inorg. Chem. 1997, 36, 2372.
205. Schenk, W. A.; Dürr, M. Chem. Eur. J. 1997, 3, 713.
206. Otto, M.; Boone, B. J.; Arif, A. M.; Gladysz, J. A. J. Chem. Soc., Dalton Trans. 2001, 1218.
207. (a) Gilman, H.; Robinson, J.; Beaber, N. J. J. Am. Chem. Soc. 1926, 48, 2715.
208. Gilman, H.; Robinson, J. Bull. Soc. Chim. Fr. 1929, 45, 636.
209. Andersen, K. K. Tetrahedron Lett. 1962, 93.
210. (a) Andersen, K. K.,; Gaffield, W.; Papanikolaou, N. E.; Foley, J. W.; Perkins, R. I. J. Am. Chem. Soc. 1964, 86, 5637.
211. (b) Andersen, K. K. Int. J. Sulfur Chem. 1971, 6, 69.
212. (a) Alexrod, M.; Bickert, P.; Jacobus, J.; Green, M.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4835.
213. (b) Nishio, M.; Nishihata, K. J. Chem. Soc., Chem. Commun. 1970, 1485.
214. (c) Juge, S.; Kagan, H. B. Tetrahedron Lett. 1975, 2733.
215. Mislow, K.; Ternay, A.; Melillo, J. T. J. Am. Chem. Soc. 1963, 85, 2329.
216. (a) Mioskowski, C.; Solladié, G. Tetrahedron 1980, 36, 227.
217. Mioskowski, C.; Solladié, G. Tetrahedron Lett. 1975, 3341.
218. Solladié, G.; Hutt, J.; Girardin, A. Synthesis 1987, 173.
219. Drabowicz, J.; Kielbasinski, P.; Mikolajczyk, M. In The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappaport, Z., Stirling, C., Eds.; Wiley and Sons: New York, 1988; Chapter 8.
220. Wudl, F.; Lee, T. B. K. J. Am. Chem. Soc. 1973, 95, 6349.
221. Benson, S. C.; Snider, J. K. Tetrahedron Lett. 1991, 32, 5885.
222. Han, Z.; Krishnamurthy, D.; Grover, P.; Fang, Q. K.; Senanayake, C. H. J. Am. Chem. Soc. 2002, 124, 7880.
223. (a) Van Woerden, H. F. Chem. Rev. 1963, 557 and references therein.
224. (b) Andersen, K. K. In Comprehensive Organic Chemistry; Barto, D., Ollis, W. D., Eds.; Pergamon Press: Oxford, 1979; Vol. 3, p 367.
225. Rebiere, F.; Kagan, H. B. Tetrahedron Lett. 1989, 30, 3659.
226. Rebiere, F.,; Samuel, O.; Ricard, L.; Kagan, H. B. J. Org. Chem. 1991, 56, 5991.
227. (a) Rebiere, F.; Riant, O.; Kogan, H. B. Tetrahedron: Asymmetry 1990, 1, 199.
228. (b) Devant, R.; Malher, U.; Braon, M. Chem. Ber. 1988, 121, 397.
229. Mikolaczyk, M.; Drabowicz, J. Synthesis 1974, 124.
230. Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568.
231. Mase, N.; Watanabe, Y.; Toru, T. J. Org. Chem. 1998, 63, 3899.
232. For an excellent review on the synthesis and synthetic applications of sulfinyl chlorides, see: Schwan, A. L.; Stricker, R. R. Org. Prep. Proc. Int. 1999, 31, 579.
233. Yoon, J.-H.; Hermann, R. Tetrahedron Lett. 1986, 27, 1493.
234. (b) Yoon, J.-H.; Hermann, R. Synthesis 1987, 72.
235. Block, E.; O'Connor, J. J. Am. Chem. Soc. 1974, 96, 3921.
236. Netscher, T.; Prinzbach, H. Synthesis 1987, 683.
237. Whitesell, J. K.; Chen, H. H.; Lawrence, R. M. J. Org. Chem. 1985, 50, 4663.
238. Whitesell, J. K. Chem. Rev. 1992, 92, 953.
239. Whitesell, J. K.; Wong, M.-S. J. Org. Chem. 1991, 56, 4552.
240. Whitesell, J. K.; Wong, M.-S. J. Org. Chem. 1994, 59, 597.
241. Evans, D. A.; Kañdor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 701.
242. Evans, D. A.; Faul, M. M.; Colombo, L.; Bisaha, J. J.; Clardy, J., Cherry, D. J. Am. Chem. Soc. 1992, 114, 5977.
243. Marino, J. P.; Bogdan, S.; Kimura, K. J. Am. Chem. Soc. 1992, 114, 5566.
244. Alonso, R.; García Ruano, J. L.; Noheda, P.; Zarzuelo, M. M. Tetrahedron: Asymmetry 1995, 6, 1133.
245. Bueno, A. B.; Carreño, M. C.; García Ruano, J. L.; Gómez Arrayás, R.; Zarzuelo, M. M. J. Org. Chem. 1997, 62, 2139.
246. Oppolzer, W. Pure Appl. Chem. 1990, 62, 1241.
247. Oppolzer, W.; Froelich, O.; Wiaux-Zamar, C.; Bernardinelli, G. Tetrahedron Lett. 1997, 38, 2825.
248. Davis, F. A.; Zhou, P.; Reddy, G. V.; Chem. Soc. Rev. 1998, 27, 13.
249. Fernández, I.; Khiar, N.; Llera, J. M.; Alcudia, F. J. Org. Chem. 1992, 57, 6789.
250. (a) Ridley, D. D.; Smal, M. A. J. Chem. Soc., Chem. Commun. 1981, 505.
251. (b) Ridley, D. D.; Smal, M. A. Aust. J. Chem. 1982, 35, 495.
252. Alcudia, F.; Fernández, I.; Khiar, N.; Llera, J. M. Phosphorus, Sulfur Silicon Relat. Elements 1993, 74, 309.
253. Khiar,N.; Fernández, I. Alcudia, F. Phosphorus, Sulfur Silicon Relat. Elements 1993, 73, 405.
254. Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1994, 35, 5719
255. Khiar, N.; Araújo, S. C.; Alcudia, F.; Fernández, I. J. Org. Chem. 2002, 67, 345.
256. Fernández, I.; Khiar, N.; Roca, A.; Benabra, A.; Alcudia, A.; Espartero, J. L.; Alcudia, F. Tetrahedron Lett. 1999, 40, 2029.
257. Khiar, N.; Alcudia, F.; Espartero, J.-L.; Rodríguez, L.; Fernández, I. J. Am. Chem. Soc. 2000, 122, 7598.
258. Berry, R. S. J. Chem. Phys. 1960, 32, 933.
259. For good discussion on the stereochemical outcome of nucleophilic substitution on a tricoordinated sulfur atom, see: Okuyama, T. In The Chemistry of Sulphinic Acids, Esters and Their Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, England, 1990; Chapter 21.
260. (a) Rautenstrauch, V. Bull. Soc. Chim. Fr. 1994, 515.
261. (b) Soai, K.; Hori, H.; Kawahara, M. J. Chem. Soc., Chem. Commun. 1992, 106.
262. (c) Baba, S. E.; Sartor, K.; Poulin, J.-C.; Kagan, H. B. Bull. Soc. Chim. Fr. 1994, 525.
263. (a) Sulfurane as intermediate: Martin, J. C.; Paul, I. C. Science 1976, 191, 154.
264. (b) Hayes, R. A.; Martin, J. C. In Organic Sulfur Chemistry, Theoretical and Experimental Advances; Bernardi, F., Csimadia, I. G., Mangini, A., Eds.; Elsevier; Amsterdam, 1985; Chapter 8.
265. (c) Oae, S. Reviews on Heteroatom Chemistry; MYO: Tokyo, 1988; Vol. 1, p. 304.
266. (d) Furokawa, N. In Heteroatom Chemistry; Block, E., Ed.; VCH: New York, 1990; p 165.
267. Benabra, A.; Alcudia, A.; Fernández, I.; Khiar, N.; Alcudia, F. Tetrahedron: Asymmetry 1996, 7, 3353.
268. Khiar, N.; Fernández, I.; Alcudia, F.; Hua, D. H. Tetrahedron Lett. 1993, 34, 699.
269. El Ouazzani, H.; Khiar, N.; Fernández, I.; Alcudia, F. J. Org. Chem. 1997, 62, 287.
270. Krazmer, J. S.; Daddona, P. E.; Dalke, A. P.; Kelly, W. N. Biochem. Pharmacol. 1983, 32, 805.
271. Arroyo-Gómez, Y.; López-Sastre, J. A.; Rodríguez-Amo, J. F.; Sántos-García, M.; Sanz-Tejedor, M. A. J. Chem. Soc., Perkin Trans. 1 1994, 2177.
272. Díaz Bueno, N.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129.
273. García Ruano, J. L.; Fernández, I.; del Prado Catalina, M.; Alcudia Cruz, A. Tetrahedron: Asymmetry 1996, 7, 3407.
274. Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011.
275. (a) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464.
276. (b) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794.
277. Mase, N.; Watanabe, Y.; Toru, T. J. Org. Chem. 1998, 63, 3899.
278. Gautier, N.; Noiret, N.; Nugier-Chauvin, C.; Patin, H. Tetrahedron: Asymmetry 1997, 8, 501.
279. (a) Alayrac, C.; Nowaczyk, S.; Lemarié, M.; Metzner, P. Synthesis 1999, 669.
280. (b) Nowaczyk, S.; Alayrac, C.; Reboul, V.; Metzner, P.; Averbouch-Pouchot, M.-T. J. Org. Chem. 2001, 66, 7841.
281. Yabuuchi, T.; Kusumi, T. J. Am. Chem. Soc. 1999, 121, 10646.
282. (a) Cardellicchio, C.; Fiandanse, V.; Naso, F. J. Org. Chem. 1992, 57, 1718.
283. (b) Cardellicchio, C.; Fiandanse, V.; Naso, F.; Scilimati, A. Tetrahedron Lett. 1992, 33, 5121.
284. Cardellicchio, C.; Iacuone, A.; Naso, F.; Tortorella, P. Tetrahedron Lett. 1996, 37, 6017.
285. Cardellicchio, C.; Fracchiolla, G.; Naso, F.; Tortorella, P. Tetrahedron 1999, 55, 525.
286. Ammunziata, M.; Capozzi, M.; Cardellicchio, C.; Fracchiolla, G.; Naso, F.; Tortorella, P. J. Am. Chem. Soc. 1999, 121, 4708.
287. Ammunziata, M.; Capozzi, M.; Cardellicchio, C.; Fracchiolla, G.; Naso, F.; Tortorella, P. J. Org. Chem. 2000, 65, 2843.
288. Fanizzi, F. P.; Alicino, V.; Cardellicio, C.; Tortilla, P.; Rourke, J. P. Chem. Commun. 2000, 673.
289. (a) Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171.
290. (b) Backes, B. J.; Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1996, 118, 3055.
291. Liu, G.; Cogan, D.; Owens, T. D.; Tang, T. P.; Ellman, J. J. Org. Chem. 1999, 64, 1278 and references therein.
292. Zhang, J.; Saito, S.; Koizumi, T. J. Am. Chem. Soc. 1998, 120, 1631.
293. Zhang, J.; Saito, S.; Koizumi, T. J. Org. Chem. 1998, 63, 9375.
294. Davies, J. A. Adv. Inorg. Chem. Radiochem. 1981, 24, 115.
295. Mestroni, G.; Alessio, E.; Sava, G.; Pacor, S.; Coluccia, M. In Metal Complexes in Cancer Chemtherapy; Keppler, B. K., Ed.; VCH Verlag: Weinheim, 1994; p 159.
296. Chan, P. K. L.; James, B. R.; Frost, D. C.; Chan, H. L.; Hu, H.-L. Can. J. Chem. 1989, 67, 508.
297. Pearson, R. G. Coord. Chem. Rev. 1990, 100, 403.
298. Kagan, H. B.; Ronnan, B. Rev. Heteroat. Chem. 1992, 7, 92.
299. Calligaris, M.; Carugo, O. Coord. Chem. Rev. 1996, 153, 83.
300. Kitching, W.; Moore, C. J.; Doddrell, D. Aust. J. Chem. 1969, 22, 1149.
301. Kitching, W.; Moore, C. J.; Doddrell, D. Inorg. Chem. 1970, 9, 541.
302. Jaswal, J. S.; Yapp, D. T. T.; Rettig, S. J.; James, B. R.; Skov, K. A. J. Chem. Soc., Chem. Commun. 1992, 1528.
303. Pettinari, C.; Pellei, M.; Cavicchio, G.; Crucianelli, M.; Panzei, W.; Colapietro, M.; Cassetta, A. Organometallics 1999, 18, 555.
304. Baldenius, K. U.; Kagan, H. B. Tetrahedron: Asymmetry 1990, 1, 597.
305. (a) James, B. R.; McMillan, R. S.; Reimer, K. J. Mol. Catal. 1976, 1, 439.
306. (b) James B. R.; McMillan, R. S. Can. J. Chem. 1977, 55, 3927.
307. Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429.
308. Alcock, N.; Brown, J. M.; Evans, P. L. J. Organomet. Chem. 1988, 356, 233.
309. Kvintovics, P.; James, B. R.; Heil, B. J. Chem. Soc., Chem. Commun. 1986, 1810.
310. Petra, D. G. L.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leewen, P. W. N. M. J. Org. Chem. 2000, 65, 3010.
311. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamnon Press: Oxford, 1991; Vol. 5, Oppolzer, W., in Chap. 4.1, and Roush, W. R., in Chap. 4.4.
312. Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
313. Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123.
314. Kuneida, N.; Nokami, J.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1976, 49, 256.
315. Owens, T. D.; Hollander, F. J.; Oliver, A. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539.
316. Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
317. Ordoñez, M.; Gureero-de la Rosa, V.; Labastida, V.; Llera, J. M. Tetrahedron: Asymmetry 1996, 7, 2675.
318. Hiroi, K.; Watanabe, K.; Abe, I.; Koseki, M. Tetrahedron Lett. 2001, 42, 7617.
319. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1050.
320. Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922.
321. Noyori, R.; Kitamura, Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
322. Carreño, M. C.; Garcia Ruano, J. L.; Maestro, M. C.; Cabreras, M. L. Tetrahedron: Asymmetry 1993, 4, 727.
323. Chelucci, G.; Berta, D.; Saba, A. Tetrahedron: Asymmetry 1997, 3843.
324. Priego, J.; Mancheño, O. G.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346.
325. (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143.
326. (b) Hayashi, T.; Yamamoto, A.; Hgihara, T.; Ito, I. Tetrahedron Lett. 1986, 27, 191.
327. (a) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron: Asymmetry 1994, 5, 1895.
328. (b) Williams, J. M. J. Synlett 1996, 705.
329. (a) Hiroi, K.; Suzuki, Y. Heterocycles 1997, 46, 77.
330. (b) Hiroi, K.; Suzuki, Y.; Abe, I.; Hasegawa, Y.; Suzuki, K. Tetrahedron: Asymmetry 1998, 9, 3797.
331. Hiroi, K.; Suzuki, Y. Tetrahedron Lett. 1998, 39, 6499.
332. Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715.
333. (a) Hiroi, K.; Suzuki, Y.; Abe, I. Chem. Lett. 1999, 150, 149.
334. (b) Hiroi, K.; Suzuki, Y.; Abe, I.; Kawagishi, R. Tetrahedron 2000, 56, 4701.
335. Tokunoh, R.; Sodeoka, M.; Abe, K.; Shibasaki, M. Tetrahedron Lett. 1995, 36, 8035.
336. Payne, S. G. Sulfur Rep. 1999, 21, 281
337. Reggellin, M.; Zur, C. Synthesis 2000, 1.
338. Johnson, C. R.; Kirchoff, R. A.; Gorkin, H. G. J. Org. Chem. 1974, 39, 2458.
339. Zehnder, M.; Bolm, C.; Schaffner, S.; Kauffmann, D.; Muller, J. Liebigs Ann. 1995, 125.
340. Bolm, C.; Muller, J.; Schlingloff, G.; Zehnder, M.; Neuburger, M. J. Chem. Soc., Chem. Commun. 1993, 182.
341. Bolm, C.; Bienewald, F.; Harms, K. Synlett. 1996, 775.
342. Bolm, C.; Felder, M. Tetrahedron Lett. 1993, 34, 6041.
343. Johnson, C. R.; Stark, C. J., Jr. Tetrahedron Lett. 1979, 34, 4713.
344. Bolm, C.; Seger, A.; Felder, M. Tetrahedron Lett. 1993, 34, 8079.
345. Bolm, C.; Felder, M. Synlett 1994, 655.
346. Bolm, C.; Müller, J. Tetrahedron 1994, 50, 4355.
347. Bolm, C.; Felder, M.: Müller, J. Synlett 1992, 439.
348. Bolm, C.; Müller, P. Tetrahedron Lett. 1995, 36, 1625.
349. Bolm, C.; Kaufmann, D.; Zehdner, M.; Neuburger, M. Tetrahedron Lett. 1996, 37, 3985.
350. Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830.
351. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994.
352. Paley, R. S.; de Dios, A.; Estroff, L. A.; Lafontaine, J. A.; Montero, C.; McCulley, D. J.; Rubio, B.; Ventura, M. P.; Weers, H.; Fernández de la Pradilla, R.; Castro, S.; Dorado, R.; Morente, M. J. Org. Chem. 1997, 62, 6326.
353. Paley, R. S.; Rubio, M. B.; Fernández de la Pradilla, R.; Dorado, R.; Hundal, G.; Martínez-Ripoll, M. Organometallics 1996, 15, 4672.
354. Paley, R. S.; Estroff, L. A.; McCulley, D. J.; Martínez-Cruz, L. A.; Sánchez, A. J.; Cano, F. H. Organometallics 1998, 17, 1841.
355. Paley, R. S.; Estroff, L. A.; Gauguet, J. M.; Hunt, D. K.; Newlin, R. C. Org. Lett. 2000, 2, 365.
356. (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
357. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036.
358. (a) Togni, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1475.
359. (b) Ferrocenes; Hayashi, T., Togni, A., Eds.; VCH: Weinheim, 1995.
360. (a) Marquarding, D.; Klusacek, H.; Gokeh, G. W.; Hoffmann, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389.
361. (b) Gokel, G. W.; Ugi, I. K. J. Chem. Educ. 1972, 49, 294.
362. Hua, D. H.; Lagneau, N. M.; Chen, Y.; Robber, P. M.; Clapham, G.; Robinson, P. D. J. Org. Chem. 1996, 61, 4508.
363. (a) Guillaneux, D.; Kagan, H. J. Org. Chem. 1995, 60, 2502.
364. (b) Riant, O.; Argouarch, G.; Guillaneux, D.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1998, 63, 3511.
365. Bolm, C.; Muñiz, K.; Aguilar, N.; Kesselgruber, M.; Raabe, G. Synthesis 1999, 1251.
366. Griffiths, S. L.; Perrio, S.; Thomas, S. E. Tetrahedron: Asymmetry 1994, 5, 1847.
367. Davies, S.; Loveridge, T.; Clough, J. M. J. Chem. Soc., Chem. Commun. 1995, 817.
368. Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153.
369. Hiroi, K.; Onuma, H.; Arinaga, Y. Chem. Lett. 1995, 35, 1099.
370. Henrich, M.; Delgado, A.; Molins, E.; Roig, A.; Llebaria, A. Tetrahedron Lett. 1999, 40, 4259.
371. Villar, J. M.; Delgado, A.; Llebaría, A.; Moretó, J. M.; Molins, E.; Miravitles, C. Tetrahedron 1996, 52, 10525-1546.
372. Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
373. (a) Diaz Buezo, N.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129.
374. Priego, J.; Carretero, J. C. Synlett 1999, 1603.
375. (a) Pauson, P. L.; Khand, I. U. Ann. N.Y. Acad. Sci. 1977, 295, 2.
376. (b) Schore, N. E. Org. React. 1991, 40, 1.
377. Montenegro, E.; Moyano, A.; Pericás, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. Tetrahedron: Asymmetry 1999, 10, 457.
378. Adrio, J.; Carretero, J. C. J. Am. Chem. Soc. 1999, 121, 7411.
379. For an excellent review on combinatorial synthesis of small molecules, see: Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lasky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288.
380. For a recent review of solid-phase linkers, see: James, I. W. Tetrahedron 1999, 55, 4855.
381. Obika, S.; Nishiyama, T.; Tatematsu, S.; Nishimoto, M.; Miyashita, K.; Imanishi, T. Heterocycles 1998, 49, 261.
382. Lee, Y.; Silverman, R. B. Org. Lett. 2000, 2, 303.
383. Dragoli, D. R.; Burdett, M.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 10127.
384. Rolland, C.; Hanquet, G.; Ducep, J.; Solladié, G. Tetrahedron Lett. 2001, 42, 9077.
385. Rolland, C.; Hanquet, G.; Ducep, J.; Solladié, G. Tetrahedron Lett. 2001, 42, 7563.
386. Nakamura, S.; Uchiyama, Y.; Ishikawa, S.; Fukinbara, R.; Watanabe, Y.; Toru, T. Tetrahedron Lett. 2002, 43, 2381.
387. (a) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668.
388. (b) Luchaco-Cullis, C. A.; Mizutani, H.; Murphy, K. E.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2001, 40, 1456.
389. Fannizi, F. P.; Alicino, V.; Cardellichio, C.; Rourke, J. P. Chem. Commun. 2000, 673.
390. (a) Savage, P. B.; Holmgren, S. K.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 7900.
391. (b) Savage, P. B.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 10448 and references therein.