Around and beyond Cram's Rule

Chemical Reviews

Volumn 99, Issue 5, 1999, Pages 1191-1223

  Mengel, Anne ^a,b   Reiser, Oliver ^a,c,d  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

^c IBM ALMADEN RESEARCH CENTER   (United States)

^d HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001213599     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr980379w     Document Type: Article

References (265)

1. (1) (a) Cram, D. J.; Wilson, D. R. J. Am. Chem. Soc. 1963, 85, 1245-1249.
2. (b) Cram, D. J.; Elhafez, F. A. A. J. Am. Chem. Soc. 1952, 74, 5828-5835.
3. (c) Cram, D. J.; Greene, F. D. J. Am. Chem. Soc. 1953, 75, 6004-6010.
4. Reviews: (a) Vögtle, F.; Franke, J.; Aigner, A.; Worsch, D. Chem. Unserer Zeit 1984, 18, 203-212. (b) Mulzer, J. Nachr. Chem. Technol. Lab. 1984, 32, 16-18. (c) Mulzer, J. Organic Synthesis Highlights; VCH: Weinheim, 1991; pp 3-8. (d) Devant, R. M.; Radunz, H.-E. Formation of C-C Bonds by Addition to Carbonyl Groups; Houben-Weyl, Georg Thieme: Stuttgart/New York, 1995; E21, pp 1151-1235. (e) Mulzer, J. Diastereoface Selection (Differentiation) 1, n-Induction; Houben-Weyl, Georg Thieme: Stuttgar/New York, 1995; E21, pp 121-140. (f) Yamaguchi, M. Lewis Acid Promoted Addition Reactions of Organometallic Compounds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford/New York, 1991; Vol. 1, pp 325-353.
5. Reviews: (a) Vögtle, F.; Franke, J.; Aigner, A.; Worsch, D. Chem. Unserer Zeit 1984, 18, 203-212. (b) Mulzer, J. Nachr. Chem. Technol. Lab. 1984, 32, 16-18. (c) Mulzer, J. Organic Synthesis Highlights; VCH: Weinheim, 1991; pp 3-8. (d) Devant, R. M.; Radunz, H.-E. Formation of C-C Bonds by Addition to Carbonyl Groups; Houben-Weyl, Georg Thieme: Stuttgart/New York, 1995; E21, pp 1151-1235. (e) Mulzer, J. Diastereoface Selection (Differentiation) 1, n-Induction; Houben-Weyl, Georg Thieme: Stuttgar/New York, 1995; E21, pp 121-140. (f) Yamaguchi, M. Lewis Acid Promoted Addition Reactions of Organometallic Compounds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford/New York, 1991; Vol. 1, pp 325-353.
6. Reviews: (a) Vögtle, F.; Franke, J.; Aigner, A.; Worsch, D. Chem. Unserer Zeit 1984, 18, 203-212. (b) Mulzer, J. Nachr. Chem. Technol. Lab. 1984, 32, 16-18. (c) Mulzer, J. Organic Synthesis Highlights; VCH: Weinheim, 1991; pp 3-8. (d) Devant, R. M.; Radunz, H.-E. Formation of C-C Bonds by Addition to Carbonyl Groups; Houben-Weyl, Georg Thieme: Stuttgart/New York, 1995; E21, pp 1151-1235. (e) Mulzer, J. Diastereoface Selection (Differentiation) 1, n-Induction; Houben-Weyl, Georg Thieme: Stuttgar/New York, 1995; E21, pp 121-140. (f) Yamaguchi, M. Lewis Acid Promoted Addition Reactions of Organometallic Compounds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford/New York, 1991; Vol. 1, pp 325-353.
7. Reviews: (a) Vögtle, F.; Franke, J.; Aigner, A.; Worsch, D. Chem. Unserer Zeit 1984, 18, 203-212. (b) Mulzer, J. Nachr. Chem. Technol. Lab. 1984, 32, 16-18. (c) Mulzer, J. Organic Synthesis Highlights; VCH: Weinheim, 1991; pp 3-8. (d) Devant, R. M.; Radunz, H.-E. Formation of C-C Bonds by Addition to Carbonyl Groups; Houben-Weyl, Georg Thieme: Stuttgart/New York, 1995; E21, pp 1151-1235. (e) Mulzer, J. Diastereoface Selection (Differentiation) 1, n-Induction; Houben-Weyl, Georg Thieme: Stuttgar/New York, 1995; E21, pp 121-140. (f) Yamaguchi, M. Lewis Acid Promoted Addition Reactions of Organometallic Compounds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford/New York, 1991; Vol. 1, pp 325-353.
8. Reviews: (a) Vögtle, F.; Franke, J.; Aigner, A.; Worsch, D. Chem. Unserer Zeit 1984, 18, 203-212. (b) Mulzer, J. Nachr. Chem. Technol. Lab. 1984, 32, 16-18. (c) Mulzer, J. Organic Synthesis Highlights; VCH: Weinheim, 1991; pp 3-8. (d) Devant, R. M.; Radunz, H.-E. Formation of C-C Bonds by Addition to Carbonyl Groups; Houben-Weyl, Georg Thieme: Stuttgart/New York, 1995; E21, pp 1151-1235. (e) Mulzer, J. Diastereoface Selection (Differentiation) 1, n-Induction; Houben-Weyl, Georg Thieme: Stuttgar/New York, 1995; E21, pp 121-140. (f) Yamaguchi, M. Lewis Acid Promoted Addition Reactions of Organometallic Compounds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford/New York, 1991; Vol. 1, pp 325-353.
9. Reviews: (a) Vögtle, F.; Franke, J.; Aigner, A.; Worsch, D. Chem. Unserer Zeit 1984, 18, 203-212. (b) Mulzer, J. Nachr. Chem. Technol. Lab. 1984, 32, 16-18. (c) Mulzer, J. Organic Synthesis Highlights; VCH: Weinheim, 1991; pp 3-8. (d) Devant, R. M.; Radunz, H.-E. Formation of C-C Bonds by Addition to Carbonyl Groups; Houben-Weyl, Georg Thieme: Stuttgart/New York, 1995; E21, pp 1151-1235. (e) Mulzer, J. Diastereoface Selection (Differentiation) 1, n-Induction; Houben-Weyl, Georg Thieme: Stuttgar/New York, 1995; E21, pp 121-140. (f) Yamaguchi, M. Lewis Acid Promoted Addition Reactions of Organometallic Compounds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford/New York, 1991; Vol. 1, pp 325-353.
10. First direct observation of Cram-Chelate transition states, see: (a) Reetz, M. T.; Huellmann, M.; Seitz, T. Angew. Chem. 1987, 99, 478-480; Angew. Chem., Int. Ed. Engl. 1987, 26, 477. (b) Reetz, M. T.; Raguse, B.; Seitz, T. Tetrahedron 1993, 49, 8561- 8568.
11. First direct observation of Cram-Chelate transition states, see: (a) Reetz, M. T.; Huellmann, M.; Seitz, T. Angew. Chem. 1987, 99, 478-480; Angew. Chem., Int. Ed. Engl. 1987, 26, 477. (b) Reetz, M. T.; Raguse, B.; Seitz, T. Tetrahedron 1993, 49, 8561- 8568.
12. First direct observation of Cram-Chelate transition states, see: (a) Reetz, M. T.; Huellmann, M.; Seitz, T. Angew. Chem. 1987, 99, 478-480; Angew. Chem., Int. Ed. Engl. 1987, 26, 477. (b) Reetz, M. T.; Raguse, B.; Seitz, T. Tetrahedron 1993, 49, 8561-8568.
13. Review: Reetz, M. T. Acc. Chem. Res. 1993, 26, 462-468.
14. Substituents being able to form attractive interactions to other groups, e.g., OH, OMe, have been called active volume, while substituents being repulsive to other groups, e.g., OTBS, alkyl, etc., have been called passive volume. Winterfeldt, E. Stereo-selektive Synthese. Prinzipien und Methoden; Friedr. Vieweg & Sohn: Braunschweig/Wiesbaden, 1988.
15. We use "Felkin product" to refer to the Cram- or Felkin-Anh product and "anti-Felkin product" to refer to the Cram-chelate or anti-Felkin-Anh product.
16. Cornforth, J. W.; Cornforth, M. R. H.; Mathew, K. K. J. Chem. Soc. 1959, 112-127.
17. Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 18, 2199-2204.
18. (a) Anh, N. T. Top. Curr. Chem. 1980, 88, 145-162.
19. (b) Anh, N. T.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61-70.
20. (c) Anh, N. T.; Eisenstein, O. Tetrahedron Lett. 1976, 3, 155-158.
21. (a) Bürgi, H. B.; Dunitz, J. D.; Shefter, E. J. Am. Chem. Soc. 1973, 95, 5065-5067.
22. (b) Bürgi, H. B.; Dunitz, J. D.; Lehn, J. M.; Wipff, G. Tetrahedron 1974, 30, 1561-1572.
23. (c) Bürgi, H. B.; Dunitz, J. D. Acc. Chem. Res. 1983, 16, 153-161.
24. (a) Eisenstein, O.; Hoffmann, R. J. Am. Chem. Soc. 1980, 102, 6148-6149.
25. (b) Anh, N. T.; Eisenstein, O.; Lefour, J.-M.; Dâu, M.-E. T. H. J. Am. Chem. Soc. 1973, 95, 6146-6147.
26. Similar results: Fraser, R. R.; Stanciulescu, M. J. Am. Chem. Soc. 1987, 109, 1580-1581.
27. (a) Karabotsos, G. J. Tetrahedron Lett. 1972, 52, 5289-5292.
28. (b) Karabatsos, G. J.; Althuis, T. H. Tetrahedron Lett. 1967, 49, 4911-4914.
29. (c) Karabatsos, G. J. J. Am. Chem. Soc. 1967, 89, 1367-1371.
30. (a) Yamamoto, Y.; Maruyama, K. J. Am. Chem. Soc. 1985, 107, 6411-6413.
31. (b) Nakada, M.; Urano, Y.; Kobayashi, S.; Ohno, M. J. Am. Chem. Soc. 1988, 110, 4826-27.
32. (c) Molander, G. A.; Burkhardt, E. R.; Weinig, P. J. Org. Chem. 1990, 55, 4990-91.
33. (d) Greeves, N.; Lyford, L.; Pease, J. E. Tetrahedron Lett. 1994, 35, 285-288.
34. (e) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. 1992, 104, 333-334; Angew. Chem., Int. Ed. Engl. 1992, 31, 342.
35. (e) Reetz, M. T.; Harmat, N.; Mahrwald, R. Angew. Chem. 1992, 104, 333-334; Angew. Chem., Int. Ed. Engl. 1992, 31, 342.
36. (f) Maruoka, K.; Itoh, T.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 4573-4576.
37. (g) Maruoka, K.; Ttoh, T.; Sakurai, M.; Nonoshita, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 3588-3597.
38. (h) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-1454.
39. (i) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R. Angew. Chem. 1980, 92, 1044-45.
40. (j) Matsuzawa, S.; Isaka, M.; Nakamura, E. Tetrahedron Lett. 1989, 30, 1975-1978.
41. (k) Huenig, S.; Marschner, C. Chem. Ber. 1989, 122, 1329-1340.
42. (l) Yamamoto, Y.; Matsuoka, K. J. Chem. Soc., Chem. Commun. 1987, 923-924.
43. (m) Krause, N.; Seebach, D. Chem. Ber. 1987, 120, 1845-51.
44. (n) Yamamoto, Y. J. Am. Chem. Soc. 1988, 110, 4475-4476.
45. (o) Cram, D. J.; Elhafez, F. A. A.; Weingartner, H. J. Am. Chem. Soc. 1953, 75, 2293-97.
46. (p) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-54.
47. (r) Cram, D. J.; Elhafez, F. A. A.; Nyquist, H. L. J. Am. Chem. Soc. 1954, 76, 22-28.
48. (s) Cram, D. J.; Ejhafez, F. A. A.; Nyquist, H. L. J. Am. Chem. Soc. 1954, 76, 22-28.
49. (t) Midland, M. M.; Kwon, Y. C. J. Am. Chem. Soc. 1983, 105, 3725-3727.
50. (u) Kunz, T.; Reissig, H.-U. Liebigs Ann. Chem. 1989, 891-894.
51. (v) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Organomet. Chem. 1985, 285, 31-42.
52. (w) Reetz, M. T.; Steinbach, R.; Westermann, J.; Urz, R.; Wenderoth, B.; Peter, R. Angew. Chem. 1982, 94, 133-134; Angew. Chem., Int. Ed. Engl. 1982, 27, 135.
53. (w) Reetz, M. T.; Steinbach, R.; Westermann, J.; Urz, R.; Wenderoth, B.; Peter, R. Angew. Chem. 1982, 94, 133-134; Angew. Chem., Int. Ed. Engl. 1982, 27, 135.
54. (x) Rahman, A. U.; Shah, Z. In Stereoselective Synthesis in Organic Chemistry; Springer-Verlag: New York, 1993; pp 168-169.
55. (y) Toda, F.; Tanaka, K.; Mori, K. Chem. Lett. 1983, 827-830.
56. (z) Frenking, G.; Köhler, K. F.; Reetz, M. T. Tetrahedron 1991, 47, 9005-18.
57. (a) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265-268.
58. (b) Henry, K. J.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett. 1992, 33, 1817-1820.
59. (c) Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863-6866.
60. (d) Paquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1995, 118, 1931-1937.
61. (e) Mead, K.; Macdonald, T. L. J. Org. Chem. 1985, 50, 422-24
62. (f) Still, W. C.; Schneider, J. A. Tetrahedron Lett. 1980, 21, 1035-38.
63. (g) Still, W. C.; Schneider, J. A. Tetrahedron Lett. 1980, 21, 1031-34.
64. (h) Samuels, W. D.; Nelson, D. A.; Hallen, R. T. Tetrahedron Lett. 1986, 27, 3091-3094.
65. (i) Nakata, T.; Tanaka, T.; Oishi, T. Tetrahedron Lett. 1983, 24, 2653-2656.
66. (j) Shibata, I.; Yoshida, T.; Kawakami, T.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 4049-4051.
67. (k) Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1990, 112, 6130-6131.
68. (l) Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778-1784.
69. (m) Mulzer, J.; Kattner, L.; Strecker, A. R.; Schröder, C.; Buschmann, J.; Lehmann, C.; Luger, P. J. Am. Chem. Soc. 1991, 113, 4218-29.
70. (n) Reetz, M. T.; Huellmann, M. J. Chem. Soc., Chem. Commun. 1986, 21, 1600-1602.
71. (o) Stocker, J. H.; Sidisunthorn, P.; Benjamin, B. M.; Collins, C. J. J. Am. Chem. Soc. 1960, 82, 3913-18.
72. (p) Reetz, M. T.; Drewer, M. W.; Schmitz, A. Angew. Chem. 1987, 99, 1186-1188; Angew. Chem., Int. Ed. Engl. 1987, 26, 1141.
73. (p) Reetz, M. T.; Drewer, M. W.; Schmitz, A. Angew. Chem. 1987, 99, 1186-1188; Angew. Chem., Int. Ed. Engl. 1987, 26, 1141.
74. (q) Barbaro, G.; Battaglia, A.; Giorgianni, P. Tetrahedron 1993, 49, 4293-4306.
75. (r) Fujita, M.; Hiyama, T. J. Org. Chem. 1988, 53, 5415-5421.
76. (s) Buckley, T. F.; Rapoport, H. J. Am. Chem. Soc. 1981, 103, 6157-6163.
77. (t) Cokley, T. M.; Isaacs, N. S.; McCluskey, A.; Young, D. J. Main Group Metal Chem. 1997, 20, 581-582.
78. (u) Hormuth, S.; Reissig, H.-U.; Dorsch, D. Liebigs Ann. Chem. 1994, 121-128.
79. (v) Shimagaki, M.; Maeda, T.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1984, 25, 4775-4778.
80. (w) Nakata, T.; Oishi, T. Tetrahedron Lett. 1980, 21, 1641-1644.
81. Taniguchi, M.; Fujii, H.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1992, 33, 4353-4356.
82. (y) Taniguchi, M.; Fujii, H.; Oshima, K.; Utimoto, K. Tetrahedron 1993, 49, 11169-11182.
83. (z) Jackson, W. R.; Jacobs, H. A.; Jayatilake, G. S.; Matthews, B. R.; Watson, K. G. Aust. J. Chem. 1990, 43, 2045-2062.
84. (a) Reetz, M. T.; Steinbach, R.; Westermann, J.; Urz, R.; Wenderoth, B.; Peter, R. Angew. Chem. 1982, 94, 133-134; Angew. Chem., Int. Ed. 1982, 21, 135.
85. (a) Reetz, M. T.; Steinbach, R.; Westermann, J.; Urz, R.; Wenderoth, B.; Peter, R. Angew. Chem. 1982, 94, 133-134; Angew. Chem., Int. Ed. 1982, 21, 135.
86. (b) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799-8804.
87. (c) Paquette, L. A.; Bennett, G. D.; Isaac, M. B.; Chhatriwalla, A. J. Org. Chem. 1998, 63, 1836-1845.
88. Alvarez-Ibarra, C.; Arjona, O.; Perez-Ossorio, R.; Perez-Rubalcaba, A.; Quiroga, M. L.; Santesmases, M. J. J. Chem. Soc., Perkin Trans. 2 1983, 1645-1648.
89. (a) Yamamoto, Y.; Matsuoka, K. J. Chem. Soc., Chem. Commun. 1987, 923-924.
90. (b) Yamamoto, Y.; Yamada, J. J. Am. Chem. Soc. 1987, 109, 4395-96.
91. (c) Soai, K.; Niwa, S.; Hatanaka, T. Bull. Chem. Soc. Jpn. 1990, 63, 2129-30.
92. (a) Perez-Ossorio, R.; Perez-Rubalca, A.; Quiroga, M. L. Tetrahedron Lett. 1980, 21, 1565-1566.
93. (b) Janowitz, A.; Kunz, T.; Handke, G.; Reissig, H.-U. Synlett 1989, 24-25.
94. (c) Mead, K. T. Tetrahedron Lett. 1987, 28, 1019-1022.
95. (a) Herold, P. Helv. Chim. Acta 1988, 71, 354-362.
96. (b) Caputo, R.; Longobardo, L.; Palumbo, G.; Pedaella, S.; Giordano, F. Tetrahedron 1996, 52, 11857-11866.
97. (c) Coleman, R. S. Tetrahedron Lett. 1992, 33, 1697-1700.
98. (d) Bayquen, A. V.; Read, R. W. Tetrahedron 1996, 52, 13467-13482.
99. (e) Ageno, G.; Banfi, L.; Cascio, G.; Guanti, G.; Manghisi, E.; Riva, R.; Rocca, V. Tetrahedron 1995, 51, 8121-8134.
100. (f) Williams, L.; Zhang, Z.; Shao, F.; Carroll, P. J.; Joullie, M. M. Tetrahedron 1996, 52, 11673-11694.
101. Similar to the Garner aldehyde: Poli, G.; Maccagni, E.; Manzoni, L.; Pilati, T.; Scolastico, C. Tetrahedron 1997, 53, 1759-1776.
102. (a) Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843-2846.
103. (b) Mulzer, J.; Kappert, M.; Huttner, G.; Jibril, I. Angew. Chem. 1984, 96, 726-727; Angew. Chem., Int. Ed. Engl. 1984, 23, 704.
104. (b) Mulzer, J.; Kappert, M.; Huttner, G.; Jibril, I. Angew. Chem. 1984, 96, 726-727; Angew. Chem., Int. Ed. Engl. 1984, 23, 704.
105. (c) Mulzer, J.; Buettelmann, B.; Muench, W. Liebigs Ann. Chem. 1988, 445-448.
106. (d) Mulzer, J.; Greifenberg, S.; Beckstett, A.; Gottwald, M. Liebigs Ann. Chem. 1992, 11, 1131-1136.
107. (e) Mulzer, J.; Funk, G. Synthesis 1995, 101-112.
108. (f) Paquette, L. A.; Montgomery, F. J.; Wang, T.-Z. J. Org. Chem. 1995, 60, 7857-7864.
109. (g) Ramachandran, P. V.; Li, G.; Brown, H. C. J. Org. Chem. 1996, 61, 100-104.
110. (a) Singh, S. M.; Oehlschlager, A. C. Can. J. Chem. 1988, 66, 209-213.
111. (b) Bhupathy, M.; Cohen, T. Tetrahedron Lett. 1985, 26, 2619-2622.
112. (c) Cohen, T.; Bhupathy, M. Tetrahedron Lett. 1983, 24, 4163-64.
113. Bai, X.; Eliel, E. L. J. Org. Chem. 1992, 57, 5166-5172.
114. Ko, K.-Y.; Park, J.-Y. Tetrahedron Lett. 1997, 38, 407-410.
115. Further examples for the application of the Felkin-Anh model to cyclohexancarbaldehydes: Krafft, M. E.; Chirico, X. Tetrahedron Lett. 1994, 35, 4511-4514.
116. Felkin-Anh model in thioketone chemistry: Mori, I.; Barlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 5966-5977.
117. Yamamoto, Y.; Nishii, S.; Maruyama, K. J. Am. Chem. Soc. 1986, 108, 7778-7786.
118. Further examples for the application of the Felkin-Anh model in imine chemistry: (a) Stojanovic, A.; Renaud, P. Helv. Chim. Acta 1998, 81, 268-285. (b) Yamada, J.-I.; Sato, H.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 5611-5614. (c) Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271- 3274. (d) Cowling, M. P.; Jenkins, P. R.; Cooper, K. J. Chem. Soc., Chem. Commun. 1988, 1503-1504. (e) Wuts, P. G. M.; Jung, Y.-W. J. Org. Chem. 1991, 56, 365-372.
119. Further examples for the application of the Felkin-Anh model in imine chemistry: (a) Stojanovic, A.; Renaud, P. Helv. Chim. Acta 1998, 81, 268-285. (b) Yamada, J.-I.; Sato, H.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 5611-5614. (c) Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271- 3274. (d) Cowling, M. P.; Jenkins, P. R.; Cooper, K. J. Chem. Soc., Chem. Commun. 1988, 1503-1504. (e) Wuts, P. G. M.; Jung, Y.-W. J. Org. Chem. 1991, 56, 365-372.
120. Further examples for the application of the Felkin-Anh model in imine chemistry: (a) Stojanovic, A.; Renaud, P. Helv. Chim. Acta 1998, 81, 268-285. (b) Yamada, J.-I.; Sato, H.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 5611-5614. (c) Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271-3274. (d) Cowling, M. P.; Jenkins, P. R.; Cooper, K. J. Chem. Soc., Chem. Commun. 1988, 1503-1504. (e) Wuts, P. G. M.; Jung, Y.-W. J. Org. Chem. 1991, 56, 365-372.
121. Further examples for the application of the Felkin-Anh model in imine chemistry: (a) Stojanovic, A.; Renaud, P. Helv. Chim. Acta 1998, 81, 268-285. (b) Yamada, J.-I.; Sato, H.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 5611-5614. (c) Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271- 3274. (d) Cowling, M. P.; Jenkins, P. R.; Cooper, K. J. Chem. Soc., Chem. Commun. 1988, 1503-1504. (e) Wuts, P. G. M.; Jung, Y.-W. J. Org. Chem. 1991, 56, 365-372.
122. Further examples for the application of the Felkin-Anh model in imine chemistry: (a) Stojanovic, A.; Renaud, P. Helv. Chim. Acta 1998, 81, 268-285. (b) Yamada, J.-I.; Sato, H.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 5611-5614. (c) Williams, D. R.; Osterhout, M. H.; Reddy, J. P. Tetrahedron Lett. 1993, 34, 3271- 3274. (d) Cowling, M. P.; Jenkins, P. R.; Cooper, K. J. Chem. Soc., Chem. Commun. 1988, 1503-1504. (e) Wuts, P. G. M.; Jung, Y.-W. J. Org. Chem. 1991, 56, 365-372.
123. (a) Chérest, M.; Felkin, H.; Frajerman, C. Tetrahedron Lett. 1971, 379-82.
124. (b) Huet, J.; Maroni-Barnaud, Y.; Anh, N. T.; Seyden-Penne, J. Tetrahedron Lett. 1976, 159-62.
125. (c) Cieplak, A. S.; Tait, B. D.; Johnson, C. R. J. Am. Chem. Soc. 1989, 111, 8447-62.
126. (d) Li, H.; Noble le, W. J. Recl. Trav. Chim. Pays-Bas 1992, 111, 199-210.
127. (a) Ono, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1996, 37, 221-224.
128. (b) Bubert, C.; Reiser, O. Tetrahedron Lett. 1997, 38, 4985-4988.
129. Dauben, W. G.; Dinges, J.; Smith, T. C.; Timothy, C. J. Org. Chem. 1993, 58, 7635-7637.
130. (a) Lautens, M.; Delanghe, P. H. M. J. Org. Chem. 1995, 60, 2474-2487.
131. (b) Delanghe, P. H. M.; Lautens, M. Tetrahedron Lett. 1994, 35, 9513-9516.
132. (a) Takeda, Y.; Matsumoto, T.; Sato, F. J. Org. Chem. 1986, 51, 4728-31.
133. (b) Okamoto, S.; Tsujiyama, H.; Yoshino, T.; Sato, F. Tetrahedron Lett. 1991, 32, 5789-92.
134. (c) Howe, G. P.; Wang, S.; Procter, G. Tetrahedron Lett. 1987, 28, 2629-32.
135. Further examples in epoxid chemistry: (a) Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1991, 32, 5345-5348. (b) Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron 1993, 49, 5253-5266.
136. Further examples in epoxid chemistry: (a) Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1991, 32, 5345-5348. (b) Escudier, J.-M.; Baltas, M.; Gorrichon, L. Tetrahedron 1993, 49, 5253-5266.
137. (a) Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920-1923.
138. (b) Denmark, S. E.; Henke, B. R. J. Am. Chem. Soc. 1991, 113, 2177-2194.
139. (a) Mikami, K. Pure Appl. Chem. 1996, 68, 639-644.
140. (b) Whitesell, J. K. Formation of C-C Bonds by Pericyclic Reactions, Ene Reaction, 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Ed.; GeorgThieme Verlag: Stuttgart, 1995; Vol. E21c, pp 3271-3297.
141. (a) Cozzi, P. G.; Tagliavini, E.; UmaniRonchi, A. Gazz. Chim. Ital. 1997, 127, 247-254.
142. (b) Duthaler, R. O.; Hafner, A. Angew. Chem., Int. Ed. 1997, 36, 43-45.
143. Reviews: (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. (b) Heathcock, C. H. In Asymmetric Synthesis. Stereodifferentiating Reactions, Part B; Morrison, J. D., Ed.; AP: New York, 1984; Vol. 3, p 111. (c) Mukaiyama, T. Org. React. 1982, 28, 203.
144. Reviews: (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. (b) Heathcock, C. H. In Asymmetric Synthesis. Stereodifferentiating Reactions, Part B; Morrison, J. D., Ed.; AP: New York, 1984; Vol. 3, p 111. (c) Mukaiyama, T. Org. React. 1982, 28, 203.
145. Reviews: (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1. (b) Heathcock, C. H. In Asymmetric Synthesis. Stereodifferentiating Reactions, Part B; Morrison, J. D., Ed.; AP: New York, 1984; Vol. 3, p 111. (c) Mukaiyama, T. Org. React. 1982, 28, 203.
146. (a) Roush, W. R. J. Org. Chem. 1991, 56, 4151-4157.
147. (b) Gennari, C.; Vieth, S.; Comotti, A.; Vulpetti, A.; Goodman, J. M. Tetrahedron 1992, 48, 4439-4458.
148. (a) Heathcock, C. H.; Pirrung, M. C.; Montgomery, S. H.; Lampe, J. Tetrahedron 1981, 37, 4087-4095.
149. (b) Woodward, R. B.; et al. J. Am. Chem. Soc. 1981, 103, 3210-3213.
150. (c) Tschamber, T.; Waespe-Sarcevic, N.; Tamm, C. Helv. Chim. Acta 1986, 69, 621-625.
151. Further examples with E(O)-enolates: (a) Aggarwal, V. K.; Stuart, S. Tetrahedron Lett. 1987, 28, 1925-1928. (b) Ahmar, M.; Bloch, R.; Mandville, G.; Romain, I. Tetrahedron Lett. 1992, 33, 2501-2504.
152. Further examples with E(O)-enolates: (a) Aggarwal, V. K.; Stuart, S. Tetrahedron Lett. 1987, 28, 1925-1928. (b) Ahmar, M.; Bloch, R.; Mandville, G.; Romain, I. Tetrahedron Lett. 1992, 33, 2501-2504.
153. Further examples with Z(O)-enolates: (a) Heathcock, C. H.; White, C. T.; Morrison, J. J.; VanDerveer, D. J. Org. Chem. 1981, 46, 1296-1309. (b) Heathcock, C. H.; Young, S. D.; Hagen, J. P. J. Org. Chem. 1980, 45, 3846-3856.
154. Further examples with Z(O)-enolates: (a) Heathcock, C. H.; White, C. T.; Morrison, J. J.; VanDerveer, D. J. Org. Chem. 1981, 46, 1296-1309. (b) Heathcock, C. H.; Young, S. D.; Hagen, J. P. J. Org. Chem. 1980, 45, 3846-3856.
155. Paterson, I.; Oballa, R. M. Tetrahedron Lett. 1997, 38, 8241-8244.
156. Lodge, E. P.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 3353-3361.
157. Further examples for Aldol reactions: (a) Evans, D. A.; Gage, J. R. Tetrahedron Lett. 1980, 31, 6129-6132. (b) Dondoni, A.; Merino, P. J. Org. Chem. 1991, 56, 5294-6301.
158. Further examples for Aldol reactions: (a) Evans, D. A.; Gage, J. R. Tetrahedron Lett. 1980, 31, 6129-6132. (b) Dondoni, A.; Merino, P. J. Org. Chem. 1991, 56, 5294-6301.
159. Further examples for Mukayama-Aldol reactions: (a) Davis, A. P.; Plunkett, S. J. J. Chem. Soc., Chem. Commun. 1995, 2173-2174. (b) Saigo, K.; Kudo, K.; Hashimoto, Y.; Kimoto, H.; Hasegawa, M. Chem. Lett. 1990, 941-944.
160. Further examples for Mukayama-Aldol reactions: (a) Davis, A. P.; Plunkett, S. J. J. Chem. Soc., Chem. Commun. 1995, 2173- 2174. (b) Saigo, K.; Kudo, K.; Hashimoto, Y.; Kimoto, H.; Hasegawa, M. Chem. Lett. 1990, 941-944.
161. Example of nitro aldol reactions: Borrachero, P.; Dianez, M. J.; Estrada, M. D.; Gomez-Guillen, M.; Gomez-Sanchez, A. Carbohydr. Res. 1995, 271, 79-100.
162. Gennari, C.; Fioravanzo, E.; Bernardi, A.; Vulpetti, A. Tetrahedron 1994, 50, 8815-8826.
163. (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem. 1985, 97, 1-78; Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
164. (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem. 1985, 97, 1-78; Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
165. (b) Heathcock, C. H.; White, C. T.; Morrison, J. J.; VanDerveer, D. J. Org. Chem. 1981, 46, 1296-1309.
166. (a) Roush, W. R.; Adam, M. A.; Walts, A. E.; Harris, D. J. J. Am. Chem. Soc. 1986, 108, 3422-34.
167. (b) Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.; Park, J. C. J. Org. Chem. 1990, 55, 4109-17.
168. Mulzer, J.; Pietschmann, C.; Buschmann, J.; Luger, P. J. Org. Chem. 1997, 62, 3938-43.
169. (a) Williams, D. R.; Benbow, J. W. J. Org. Chem. 1988, 53, 4643-4644.
170. (b) Hollady, M. W.; Rich, D. H. Tetrahedron Lett. 1983, 24, 4401-4404.
171. (c) Jones, D. M.; Nilsson, B.; Szelke, M. J. Org Chem. 1993, 58, 2286-2290.
172. (d) Karlsson, J. O.; Lundblad, A.; Malm, B.; Nilsson, I.; Nitenberg, T.; Starke, I. Tetrahedron Lett. 1989, 30, 2653-2656.
173. (a) Kreuder, R.; Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035-9038.
174. (b) Rein, T.; Anvelt, J.; Soone, A.; Kreuder, R.; Wulff, C.; Reiser, O. Tetrahedron Lett. 1995, 36, 2302-2305.
175. (c) Rein, T.; Kreuder, R.; Zezschwitz, P. v.; Wulff, C.; Reiser, O. Angew Chem. 1995, 107, 1099-1102.
176. (d) Rein, T.; Kann, N.; Kreuder, R.; Gangloff, B.; Reiser, O. Angew. Chem. 1994, 106, 597-599.
177. Furuta, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1992, 863-864.
178. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
179. Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162-7166.
180. Although the analysis according to the Houk model is distinctively different from the Felkin-Anh model, we will nevertheless -in an attempt to create a unified picture - refer to adducts such as 132 as the Felkin and to adducts such as 133 as the anti-Felkin product, treating the alkene double bond analogously to a carbonyl double bond. Thus, once L, M, and S have been defined on the steric and stereoelectronic prerequisites of the reaction under investigation, the Felkin product always arises upon placing L orthogonal to and M on the same side of the double bond with the double bond being attacked anti to L (cf. Scheme 4, 9 and 10).
181. Houk, K. N.; Moses, S. R.; Wu, Y. D.; Rondan, N. G.; Jäger, V.; Schohe, R.; Fronczek, F. R. J. Am. Chem. Soc. 1984, 106, 3880-3882.
182. Houk, K. N.; Rondan, N. G.; Wu, Y.-D.; Metz, J. T.; Paddon-Row, M. N. Tetrahedron 1984, 40, 2257-2274.
183. (a) Podlech, J.; Seebach, D. Liebigs Ann. Org. Bioorg. Chem. 1995, 7, 1217-1228.
184. (b) Estermann, H.; Seebach, D. Helv. Chim. Acta 1988, 71, 1824-1840.
185. (c) Fleming, I.; Lewis, J. J. J. Chem. Soc., Perkin Trans, 1 1992, 3257-3266.
186. Arai, M.; Kawasuji, T.; Nakamura, E. J. Org. Chem. 1993, 58, 5121-5129.
187. Yamamoto, Y.; Nishii, S.; Ibuka, T. J. Chem. Soc., Chem. Commun. 1987, 1572-1573.
188. Further examples: (a) Roush, W. R.; Lesur, B. M. Tetrahedron Lett. 1983, 24, 2231-2234. (b) Ibarra, C. A.; Perez, M. S. A.; Castro, I. D.; Fernandez, M. J. J. Chem. Soc., Perkin Trans. 2 1991, 467-470. (c) Mulzer, J.; Graske, K.-D.; Shanyoor, M. Liebigs Ann. Org. Bioorg. Chem. 1996, 593-598. (d) Dorigo, A. E.; Morokuma, K. J. Chem. Soc., Chem. Commun. 1989, 1884- 1886.
189. Further examples: (a) Roush, W. R.; Lesur, B. M. Tetrahedron Lett. 1983, 24, 2231-2234. (b) Ibarra, C. A.; Perez, M. S. A.; Castro, I. D.; Fernandez, M. J. J. Chem. Soc., Perkin Trans. 2 1991, 467-470. (c) Mulzer, J.; Graske, K.-D.; Shanyoor, M. Liebigs Ann. Org. Bioorg. Chem. 1996, 593-598. (d) Dorigo, A. E.; Morokuma, K. J. Chem. Soc., Chem. Commun. 1989, 1884- 1886.
190. Further examples: (a) Roush, W. R.; Lesur, B. M. Tetrahedron Lett. 1983, 24, 2231-2234. (b) Ibarra, C. A.; Perez, M. S. A.; Castro, I. D.; Fernandez, M. J. J. Chem. Soc., Perkin Trans. 2 1991, 467-470. (c) Mulzer, J.; Graske, K.-D.; Shanyoor, M. Liebigs Ann. Org. Bioorg. Chem. 1996, 593-598. (d) Dorigo, A. E.; Morokuma, K. J. Chem. Soc., Chem. Commun. 1989, 1884- 1886.
191. Further examples: (a) Roush, W. R.; Lesur, B. M. Tetrahedron Lett. 1983, 24, 2231-2234. (b) Ibarra, C. A.; Perez, M. S. A.; Castro, I. D.; Fernandez, M. J. J. Chem. Soc., Perkin Trans. 2 1991, 467-470. (c) Mulzer, J.; Graske, K.-D.; Shanyoor, M. Liebigs Ann. Org. Bioorg. Chem. 1996, 593-598. (d) Dorigo, A. E.; Morokuma, K. J. Chem. Soc., Chem. Commun. 1989, 1884-1886.
192. (a) Asao, N.; Shimada, T.; Sudo, T.; Taukada, N.; Yazawa, K.; Gyoung, Y. S.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1997, 62, 6274-6282.
193. (b) Yamamoto, Y.; Chouman, Y.; Nishii, S.; Ibuka, T.; Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652-7660.
194. Mulzer, J.; Kappert, M. Angew. Chem. 1983, 95, 60; Angew. Chem., Int. Ed. Engl. 1983, 22, 63.
195. Mulzer, J.; Kappert, M. Angew. Chem. 1983, 95, 60; Angew. Chem., Int. Ed. Engl. 1983, 22, 63.
196. Jurczak, J.; Golebiowski, A.; Raczko, J. J. Org. Chem. 1989, 54, 2495-2496.
197. Similar results: (a) Midland, M. M.; Afonso, M. M. J. Am. Chem. Soc. 1989, 111, 4368-4371. (b) Midland, M. M.; Koops, R. W. J. Org. Chem. 1990, 55, 5058-5065. (c) Garner, P.; Ramakanth, S. J. Org. Chem. 1986, 51, 2609-2612.
198. Similar results: (a) Midland, M. M.; Afonso, M. M. J. Am. Chem. Soc. 1989, 111, 4368-4371. (b) Midland, M. M.; Koops, R. W. J. Org. Chem. 1990, 55, 5058-5065. (c) Garner, P.; Ramakanth, S. J. Org. Chem. 1986, 51, 2609-2612.
199. Similar results: (a) Midland, M. M.; Afonso, M. M. J. Am. Chem. Soc. 1989, 111, 4368-4371. (b) Midland, M. M.; Koops, R. W. J. Org. Chem. 1990, 55, 5058-5065. (c) Garner, P.; Ramakanth, S. J. Org. Chem. 1986, 51, 2609-2612.
200. Application in total synthesis: (a) Danishefsky, S. J.; De Ninno, M. P.; Chen, S.-H. J. Am. Chem. Soc. 1988, 110, 3929-3940. (b) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862-867. (c) Danishefsky, S.; Kobayashi, S.; Kerwin, J. F. J. Org. Chem. 1982, 47, 1981-1983.
201. Application in total synthesis: (a) Danishefsky, S. J.; De Ninno, M. P.; Chen, S.-H. J. Am. Chem. Soc. 1988, 110, 3929-3940. (b) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862-867. (c) Danishefsky, S.; Kobayashi, S.; Kerwin, J. F. J. Org. Chem. 1982, 47, 1981-1983.
202. Application in total synthesis: (a) Danishefsky, S. J.; De Ninno, M. P.; Chen, S.-H. J. Am. Chem. Soc. 1988, 110, 3929-3940. (b) Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862-867. (c) Danishefsky, S.; Kobayashi, S.; Kerwin, J. F. J. Org. Chem. 1982, 47, 1981-1983.
203. Casas, R.; Parella, T.; Branchadell, V.; Olivia, A.; Ortuno, R. M.; Guingant, A. Tetrahedron 1992, 48, 2659-2680.
204. Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 663-666.
205. Similar results: (a) Kozikowski, A. P.; Ghosh, A. K. J. Org. Chem. 1984, 49, 2762-2772. (b) Jäger, V.; Schohe, R. Tetrahedron Lett. 1983, 24, 5501-5504.
206. Similar results: (a) Kozikowski, A. P.; Ghosh, A. K. J. Org. Chem. 1984, 49, 2762-2772. (b) Jäger, V.; Schohe, R. Tetrahedron Lett. 1983, 24, 5501-5504.
207. Trost, B. M.; Lynch, J.; Renaut, P. Tetrahedron Lett. 1985, 26, 6313-6316.
208. Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943-3946.
209. Barbaro, G.; Battaglia, A.; Giorgianni, P. Tetrahedron 1993, 49, 4293-4306.
210. Bach, T. Synthesis 1998, 683-703.
211. (a) Takano, S.; Hatakeyama, S.; Saijo, K. Tetrahedron Lett. 1985, 26, 865-868.
212. (b) Nubbemeyer, U.; Ohrlem, R.; Gonda, J.; Ernst, B.; Bellus, D. Angew. Chem. 1991, 103, 1533-1534; Angew. Chem., Int. Ed. Engl. 1991, 30, 1465.
213. (b) Nubbemeyer, U.; Ohrlem, R.; Gonda, J.; Ernst, B.; Bellus, D. Angew. Chem. 1991, 103, 1533-1534; Angew. Chem., Int. Ed. Engl. 1991, 30, 1465.
214. Cha, J. K.; Lewis, S. C. Tetrahedron Lett. 1984, 25, 5263-5266.
215. Bruckner, R.; Priepke, H. Angew. Chem. 1988, 100, 285-286; Angew. Chem., Int. Ed. Engl. 1988, 27, 278.
216. Bruckner, R.; Priepke, H. Angew. Chem. 1988, 100, 285-286; Angew. Chem., Int. Ed. Engl. 1988, 27, 278.
217. Review on 1,2-stereocontrol in radical chemistry: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH: Weinheim, 1996; pp 164-177. (b) Linker, T.; Schmittel, M. Diastereoselektive Reaktionen acyclischer Verbindungen; Wiley-VCH: Weinheim, 1998.
218. Review on 1,2-stereocontrol in radical chemistry: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH: Weinheim, 1996; pp 164-177. (b) Linker, T.; Schmittel, M. Diastereoselektive Reaktionen acyclischer Verbindungen; Wiley-VCH: Weinheim, 1998.
219. Examples of 1,2-stereocontrol in radical chemistry: (a) Roth, M.; Damm, W.; Giese, B. Tetrahedron Lett. 1996, 37, 351-354. (b) Curran, D. P.; Sun, S. Tetrahedron 1993, 34, 6181-6184. (c) Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703-1706. (d) Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 38, 233-236.
220. Examples of 1,2-stereocontrol in radical chemistry: (a) Roth, M.; Damm, W.; Giese, B. Tetrahedron Lett. 1996, 37, 351-354. (b) Curran, D. P.; Sun, S. Tetrahedron 1993, 34, 6181-6184. (c) Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703-1706. (d) Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 38, 233-236.
221. Examples of 1,2-stereocontrol in radical chemistry: (a) Roth, M.; Damm, W.; Giese, B. Tetrahedron Lett. 1996, 37, 351-354. (b) Curran, D. P.; Sun, S. Tetrahedron 1993, 34, 6181-6184. (c) Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703-1706. (d) Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 38, 233-236.
222. Examples of 1,2-stereocontrol in radical chemistry: (a) Roth, M.; Damm, W.; Giese, B. Tetrahedron Lett. 1996, 37, 351-354. (b) Curran, D. P.; Sun, S. Tetrahedron 1993, 34, 6181-6184. (c) Renaud, P.; Carrupt, P.-A.; Gerster, M.; Schenk, K. Tetrahedron Lett. 1994, 35, 1703-1706. (d) Angelaud, R.; Landais, Y. Tetrahedron Lett. 1997, 38, 233-236.
223. (e) Haraguchi, K.; Tanaka, H.; Saito, S.; Yamaguchi, K.; Miyasaka, T. Tetrahedron Lett. 1994, 35, 9721-9724.
224. (f) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607-6608.
225. Giese, B.; Damm, W.; Dickhaut, J.; Wetterich, F.; Sun, S.; Curran, D. P. Tetrahedron Lett. 1991, 32, 6097-6100.
226. Smadja, W.; Zahouily, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 5511-5514.
227. Roth, M.; Damm, W.; Giese, B. Tetrahedron Lett. 1996, 37, 351-354.
228. Reetz, M. T. Angew. Chem. 1984, 96, 542-555; Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
229. Reetz, M. T. Angew. Chem. 1984, 96, 542-555; Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
230. Evans, D. A.; Dart, M. J.; Duffy, J. I.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322-4343.
231. Evans, D. A.; Hoveyda, A. H. J. Org. Chem. 1990, 55, 5190-5192.
232. Reetz, M. T.; Jung, A. J. Am. Chem. Soc. 1983, 105, 4833-4835.
233. Shambayati, S.; Schreiber, S. L. Comprehensive Organic Synthesis: Addition to C-X-Bonds, Part 1; Pergamon Press: New York, 1991; Vol. 10.
234. Keck, G. E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847-3849.
235. Further examples leading to trans-1,3-diols: (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578. (b) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (c) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449.
236. Further examples leading to trans-1,3-diols: (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578. (b) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (c) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449.
237. Further examples leading to trans-1,3-diols: (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578. (b) Anwar, S.; Davis, A. P. Tetrahedron 1988, 44, 3761-3770. (c) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449.
238. Further examples leading to cis-1,3-diols: (a) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-158. (b) Narasaka, K.; Pai, F.- C. Tetrahedron 1984, 40, 2233-2238. (c) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467-6470. (d) Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem Lett. 1987, 1923-1926. (e) Bonadies, F.; DiFabio, R.; Gubioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703-706. (f) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (g) Kathawala, F. G.; Prager, B.; Prasad, K.; Repic, O.; Shapiro, M. J.; Stabler, R. S.; Widler, L. Helv. Chim. Acta 1986, 69, 803-805. (h) Narasaka, K.; Pai, F.-C. Chem. Lett. 1980, 1415-1418.
239. Further examples leading to cis-1,3-diols: (a) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-158. (b) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233-2238. (c) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467-6470. (d) Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem Lett. 1987, 1923-1926. (e) Bonadies, F.; DiFabio, R.; Gubioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703-706. (f) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (g) Kathawala, F. G.; Prager, B.; Prasad, K.; Repic, O.; Shapiro, M. J.; Stabler, R. S.; Widler, L. Helv. Chim. Acta 1986, 69, 803-805. (h) Narasaka, K.; Pai, F.-C. Chem. Lett. 1980, 1415-1418.
240. Further examples leading to cis-1,3-diols: (a) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-158. (b) Narasaka, K.; Pai, F.- C. Tetrahedron 1984, 40, 2233-2238. (c) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467-6470. (d) Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem Lett. 1987, 1923-1926. (e) Bonadies, F.; DiFabio, R.; Gubioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703-706. (f) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (g) Kathawala, F. G.; Prager, B.; Prasad, K.; Repic, O.; Shapiro, M. J.; Stabler, R. S.; Widler, L. Helv. Chim. Acta 1986, 69, 803-805. (h) Narasaka, K.; Pai, F.-C. Chem. Lett. 1980, 1415-1418.
241. Further examples leading to cis-1,3-diols: (a) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-158. (b) Narasaka, K.; Pai, F.- C. Tetrahedron 1984, 40, 2233-2238. (c) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467-6470. (d) Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem Lett. 1987, 1923-1926. (e) Bonadies, F.; DiFabio, R.; Gubioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703-706. (f) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (g) Kathawala, F. G.; Prager, B.; Prasad, K.; Repic, O.; Shapiro, M. J.; Stabler, R. S.; Widler, L. Helv. Chim. Acta 1986, 69, 803-805. (h) Narasaka, K.; Pai, F.-C. Chem. Lett. 1980, 1415-1418.
242. Further examples leading to cis-1,3-diols: (a) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-158. (b) Narasaka, K.; Pai, F.- C. Tetrahedron 1984, 40, 2233-2238. (c) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467-6470. (d) Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem Lett. 1987, 1923-1926. (e) Bonadies, F.; DiFabio, R.; Gubioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703-706. (f) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (g) Kathawala, F. G.; Prager, B.; Prasad, K.; Repic, O.; Shapiro, M. J.; Stabler, R. S.; Widler, L. Helv. Chim. Acta 1986, 69, 803-805. (h) Narasaka, K.; Pai, F.-C. Chem. Lett. 1980, 1415-1418.
243. Further examples leading to cis-1,3-diols: (a) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-158. (b) Narasaka, K.; Pai, F.- C. Tetrahedron 1984, 40, 2233-2238. (c) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467-6470. (d) Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem Lett. 1987, 1923-1926. (e) Bonadies, F.; DiFabio, R.; Gubioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703-706. (f) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (g) Kathawala, F. G.; Prager, B.; Prasad, K.; Repic, O.; Shapiro, M. J.; Stabler, R. S.; Widler, L. Helv. Chim. Acta 1986, 69, 803-805. (h) Narasaka, K.; Pai, F.-C. Chem. Lett. 1980, 1415-1418.
244. Further examples leading to cis-1,3-diols: (a) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-158. (b) Narasaka, K.; Pai, F.- C. Tetrahedron 1984, 40, 2233-2238. (c) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467-6470. (d) Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem Lett. 1987, 1923-1926. (e) Bonadies, F.; DiFabio, R.; Gubioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703-706. (f) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (g) Kathawala, F. G.; Prager, B.; Prasad, K.; Repic, O.; Shapiro, M. J.; Stabler, R. S.; Widler, L. Helv. Chim. Acta 1986, 69, 803-805. (h) Narasaka, K.; Pai, F.-C. Chem. Lett. 1980, 1415-1418.
245. Further examples leading to cis-1,3-diols: (a) Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-158. (b) Narasaka, K.; Pai, F.- C. Tetrahedron 1984, 40, 2233-2238. (c) Hanamoto, T.; Hiyama, T. Tetrahedron Lett. 1988, 29, 6467-6470. (d) Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem Lett. 1987, 1923-1926. (e) Bonadies, F.; DiFabio, R.; Gubioti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703-706. (f) Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012. (g) Kathawala, F. G.; Prager, B.; Prasad, K.; Repic, O.; Shapiro, M. J.; Stabler, R. S.; Widler, L. Helv. Chim. Acta 1986, 69, 803-805. (h) Narasaka, K.; Pai, F.-C. Chem. Lett. 1980, 1415-1418.
246. Priepke, H.; Weigand, S.; Brueckner, R. Liebigs Ann. 1997, 8, 1635-1644.
247. Hanessian, S.; Schaum, R. Tetrahedron Lett. 1997, 38, 163-166.
248. (a) Leitereg, T. J.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 4011-4018.
249. (b) Leitereg, T. J.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 4019-4026.
250. (c) Reetz, M. T.; Kesseler, K.; Jung, A. Tetrahedron Lett. 1984, 25, 729-732.
251. Evans, D. A.; Duffy, J. L.; Dart, M. J. Tetrahedron Lett. 1994, 35, 8537-8540.
252. Further 1,3-inductions with aldehydes: Mulzer, J.; Pietschmann, C. J. Org. Chem. 1997, 62, 3938-3943.
253. 1,3-Induction in total synthesis: (a) Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601. (b) Yamamoto, Y.; Chouman, Y.; Nishii, S.; Ibuka, T.; Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652-7660.
254. 1,3-Induction in total synthesis: (a) Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601. (b) Yamamoto, Y.; Chouman, Y.; Nishii, S.; Ibuka, T.; Kitahara, H. J. Am. Chem. Soc. 1992, 114, 7652-7660.
255. Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G.; Livingston, A. B. J. Am. Chem. Soc. 1995, 117, 6619-6620.
256. Further combinations of 1,2- and 1,3-induction: (a) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 3769-3771. (b) Cirillo, P. F.; Panek, J. S. J. Org. Chem. 1990, 55, 6071- 6073.
257. Further combinations of 1,2- and 1,3-induction: (a) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 3769-3771. (b) Cirillo, P. F.; Panek, J. S. J. Org. Chem. 1990, 55, 6071-6073.
258. Evans, D. A.; Dart, M. J.; Duffy, J. L.; Rieger, D. L. J. Am. Chem. Soc. 1995, 117, 9073-74.
259. 1,3-Inductions with ketones: (a) Nakada, M.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1994, 35, 741-744. (b) Evans, D. A.; Bartroli, O.; Godel, T. Tetrahedron Lett. 1982, 23, 4577-4580. (c) Fleming, I.; Lawrence, N. J. J. Chem. Soc., Perkin Trans. 1 1992, 3309-3326. (d) Evans, D. A.; Dart, M. J.; Duffy, J. L. Tetrahedron Lett. 1994, 35, 8541-8544.
260. 1,3-Inductions with ketones: (a) Nakada, M.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1994, 35, 741-744. (b) Evans, D. A.; Bartroli, O.; Godel, T. Tetrahedron Lett. 1982, 23, 4577-4580. (c) Fleming, I.; Lawrence, N. J. J. Chem. Soc., Perkin Trans. 1 1992, 3309-3326. (d) Evans, D. A.; Dart, M. J.; Duffy, J. L. Tetrahedron Lett. 1994, 35, 8541-8544.
261. 1,3-Inductions with ketones: (a) Nakada, M.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1994, 35, 741-744. (b) Evans, D. A.; Bartroli, O.; Godel, T. Tetrahedron Lett. 1982, 23, 4577-4580. (c) Fleming, I.; Lawrence, N. J. J. Chem. Soc., Perkin Trans. 1 1992, 3309-3326. (d) Evans, D. A.; Dart, M. J.; Duffy, J. L. Tetrahedron Lett. 1994, 35, 8541-8544.
262. 1,3-Inductions with ketones: (a) Nakada, M.; Urano, Y.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1994, 35, 741-744. (b) Evans, D. A.; Bartroli, O.; Godel, T. Tetrahedron Lett. 1982, 23, 4577-4580. (c) Fleming, I.; Lawrence, N. J. J. Chem. Soc., Perkin Trans. 1 1992, 3309-3326. (d) Evans, D. A.; Dart, M. J.; Duffy, J. L. Tetrahedron Lett. 1994, 35, 8541-8544.
263. (a) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Merino, P. Tetrahedron 1990, 46, 6167-6184.
264. (b) Reetz, M. T.; Kessler, K.; Schmidtberger, S.; Wenderoth, B.; Steinbach, R. Angew. Chem. 1983, 95, 1007-1008; Angew. Chem., Int. Ed. Engl. 1983, 22, 989.
265. (b) Reetz, M. T.; Kessler, K.; Schmidtberger, S.; Wenderoth, B.; Steinbach, R. Angew. Chem. 1983, 95, 1007-1008; Angew. Chem., Int. Ed. Engl. 1983, 22, 989.