Iron-mediated allylic substitution reactions with chirality transfer. Stereochemistry of the formation of diastereo- and enantiomerically enriched olefinic and allylic tetracarbonyl iron complexes

Organometallics

Volumn 20, Issue 21, 2001, Pages 4312-4332

  Enders, Dieter ^a   Jandeleit, Bernd ^a,b   Von Berg, Stefan ^a,c   Raabe, Gerhard ^a   Runsink, Jan ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b XenoPort Inc   (United States)

^c ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC TETRACARBONYL IRON COMPLEXES; CHIRALITY TRANSFER; ENANTIOMERICALLY ENRICHED OLEFINIC IRON COMPLEXES; IRON MEDIATED ALLYLIC SUBSTITUTION REACTIONS;

ADDITION REACTIONS; CHEMICAL BONDS; COMPLEXATION; CRYSTALLIZATION; IRON COMPOUNDS; ISOMERIZATION; MIXTURES; MOLECULAR STRUCTURE; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

ORGANOMETALLICS;

EID: 0035889187     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010343l     Document Type: Article

References (240)

1. General references for the use of transition metals and organometallics in organic synthesis: (a) Tsuji, J. Transition Metal Reagents and Catalysts; John Wiley & Sons: New York, 2000.
2. (b) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules, 2nd ed.; University Science Books: Sausalito, 1999.
3. (c) Beller, M.; Bolm, C. Transition Metals for Organic Synthesis; Wiley-VCH: Weinheim, 1998.
4. (d) Schlosser, M. Organometallics in Synthesis: A Manual; John Wiley & Sons: New York, 1996.
5. (e) Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 2nd ed.; John Wiley & Sons: New York, 1994.
6. (f) Elschenbroich, C.; Salzer, A. Organometallics; Wiley-VCH: Weinheim, 1992.
7. (g) Harrington, P. J. Transition Metals in Total Synthesis; John Wiley & Sons: New York, 1990.
8. Applications of catalytic organotransition metal complexes in organic synthesis: (a) Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH: Weinheim, 1996.
9. (b) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross Coupling Reactions; Wiley-VCH: Weinheim, 1998.
10. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
11. (d) Ojima, I. Catalytic Asymmetric Synthesis; Wiley-VCH: Weinheim, 1993.
12. Applications of stoichiometric organotransition metal complexes in organic synthesis: (a) Comely, A. C.; Gibson (née Thomas), S. E.; Sur, S. J. Chem. Soc., Perkin Trans. 1 2000, 109.
13. (b) Comely, A. C.; Gibson (née Thomas), S. E. J. Chem. Soc., Perkin Trans. 1 1999, 223.
14. (c) Donohoe, T. J.; Harji, R. R.; Moore, P. R.; Waring, M. J. J. Chem. Soc., Perkin Trans. 1 1998, 819.
15. (d) Donohoe, T. J.; Guyo, P. M.; Moore, P. R.; Stevenson, C. A. Contemp. Org. Synth. 1997, 4, 22.
16. (e) Donohoe, T. J. Contemp. Org. Synth. 1996, 3, 1.
17. Monographs and reviews about the synthetic use of a π-allyl palladium complexes: (a) Williams, J. M. J. In Advanced Asymmetric Synthesis; Stephenson, G. R., Ed.; Chapman & Hall: London, U.K., 1996; p 299.
18. (b) Tsuji, J. In Palladium Reagents and Catalysts; Tsuji, J., Ed.; John Wiley & Sons: New York, 1995; p 290.
19. (c) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 12, p 797.
20. (d) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: Weinheim, 1993; p 325.
21. (e) Kocovsky, P.; Malkov, A. V.; Vyscovil, S.; Lloyd-Jones, G. C. Pure Appl. Chem. 1999, 71, 1425.
22. (f) Vyskocil, S.; Jaracz, S.; Smrcina, M.; Stícha, M.; Hanus, V.; Polásek, M.; Kocovsky, P. J. Org. Chem. 1998, 63, 7727.
23. (g) Johannsen, M.; Joørgensen, K. A. Chem. Rev. 1998, 98, 1689.
24. (h) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
25. Nickel: (a) Chung, K.-G.; Miyake, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1, 2000, 15.
26. (b) Nomura, N.; RajanBabu, Tetrahedron Lett. 1997, 38, 1713.
27. (c) Bricout, H.; Carpentier, J.-F.; Mortreux, A. J. Chem. Soc., Chem. Commun. 1995, 1863.
28. (d) Didiuk, M. T.; Morken Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7273.
29. (e) Kang, S. K.; Cho, D. G.; Park, C. H.; Namkoong, E. Y.; Shin, J. S. Synth. Commun. 1995, 25, 1659.
30. (f) Kobayashi, Y.; Ikeda, E. J. Chem. Soc., Chem. Commun. 1994, 1789.
31. (g) Indolese, A. F.; Consiglio, G. Organometallics 1994, 13, 2230.
32. (h) Consiglio, G.; Indolese, A. F. Organometallics 1991, 10, 3425.
33. (i) Consiglio, G.; Indolese, A. F. J. Organomet. Chem. 1991, 417, C36.
34. Ruthenium: (a) Morisaki, Y.; Kondo, T.; Misudo, T.-A. Organometallics 1999, 18, 4742.
35. (b) Kondo, T.; Ono, H.; Satake, N.; Mitsudo, T.; Watanabe, Y. Organometallics 1995, 14, 1945.
36. (c) Zhang, S.-W.; Mitsudo, T.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1993, 450, 197.
37. Rhodium: (a) Evans, P. A.; Kennedy, L. J. Org. Lett. 2000, 2, 2213.
38. (b) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761.
39. (c) Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581.
40. (d) Evans, P. A., Nelson, J. D. Tetrahedron Lett. 1998, 39, 1725.
41. (e) Takeuchi, R.; Kitamura, N. New J. Chem. 1998, 659.
42. Iridium: (a) Takeuchi, R.; Shiga, N. Org. Lett. 1999, 2, 265.
43. (b) Bartels, B.; Helmchen, G. Chem. Commun. 1999, 741.
44. (c) Takeuchi, R.; Mashio, M. J. Am. Chem. Soc. 1998, 120, 8647.
45. (d) Takeuchi, R.; Mashio, M. Angew. Chem. 1997, 109, 268
46. Takeuchi, R.; Mashio, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 236.
47. (e) Janssen, J. P.; Helmchen, G. Tetrahedron Lett. 1997, 38, 8025.
48. Molybdenum: (a) Christopher, J. A.; Kocienski, P. J.; Kuhl, A.; Bell, R. Synlett, 2000, 463.
49. (b) Christopher, J. A.; Kocienski, P. J.; Procter, M. J. Synlett 1998, 425.
50. (c) Glorius, F.; Pfaltz, A. Org. Lett. 1999, 1, 141.
51. (d) Kocienski, P. J.; Brown, R. C. D.; Pommier, A.; Procter, M.; Schmidt, B. J. Chem. Soc., Perkin Trans. 1 1998, 9.
52. (e) Trost, B. M. Hachiya, I. J. Am. Chem. Soc. 1998, 120, 1104.
53. (f) Ward, Y. D.; Villanueva, L. A.; Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 897.
54. (g) Faller, J. W.; M. R. Mazzieri, Nguyen, J. T.; Parr, J.; Tokunaga, M. Pure Appl. Chem. 1994, 66, 1463.
55. (h) Yu, R. H.; McCallum, J. S.; Liebeskind, L. S, Organometallics 1994, 13, 1476.
56. (i) Dvorak, D.; Stary, I.; Kocovsky, P, J. Am. Chem. Soc. 1995, 117, 6130.
57. (j) Dvorakova, H.; Dvorak, D.; Kocovsky, P. Tetrahedron Lett. 1995, 36, 6351.
58. (k) Trost, B. M.; Merlic, C. A, J. Am. Chem. Soc. 1990, 112, 9590.
59. (l) Faller, J. W.; Linebarrier, D, Organometallics 1988, 7, 1670.
60. (m) Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1987, 109, 1469.
61. Tungsten: (a) Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem. 1995, 107, 534
62. Lloyd-Jones, G. C.; Pfaltz, A. Angew. Chem. Int. Ed. Engl. 1995, 34, 462.
63. (b) Frisell, H.; Åkermark, B. Organometallics 1995, 14, 534.
64. (c) Lehmann, J.; Lloyd-Jones, G. C. Tetrahedron 1995, 51, 8863.
65. (d) Trost, B. M.; Hung, M.-H. J. Am. Chem. Soc. 1987, 109, 2176.
66. (e) Trost, B. M.; Hung, M.-H. J. Am. Chem. Soc. 1984, 106, 6837.
67. (f) Trost, B. M.; Hung, M.-H. J. Am. Chem. Soc. 1983, 105, 7757.
68. Copper: (a) Persson, E. S. M.; van Klaveren, M.; Grove, D. M.; Bäckvall, J. E.; van Koten, G. Chem. Eur. J. 1995, 1, 351.
69. (b) van Klaveren, M.; Perrson, E. S. M.; del Vilar, A.; Grove, D. M.; Bäckvall, J. E.; van Koten, G. Tetrahedron Lett. 1995, 36, 3059.
70. (c) Flemming, S.; Kabbra, J.; Nickisch, K.; Westermann, J.; Mohr, J. Synlett 1995, 183.
71. (d) Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Fujii, N.; Mimura, N.; Yamamoto, Y. Angew. Chem. 1994, 106, 693
72. Ibuka, T.; Nakai, Y.; Habashita, H.; Hotta, Y.; Fujii, N.; Mimura, N.; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 652.
73. Manganese: Vaughan, W. S.; Gu, H. H.; McDaniel, K. F. Tetrahedron Lett. 1997, 38, 1885.
74. Platinum: Brown, J. M.; McIntyre, J. E. J. Chem. Soc., Perkin Trans. 2 1985, 961.
75. Iron: Zhou, B.; Xu, Y. J. Org. Chem. 1988, 53, 4421.
76. (b) Xu, Y.; Zhou, B. J. Org. Chem. 1987, 52, 974.
77. Cobalt: Iqbal, J.; Mukhopadhyay, M.; Mandal, A. K. Synlett 1997, 876.
78. (b) Mukhopadhyay, M.; Iqbal, J. Tetrahedron Lett 1995, 36, 6761.
79. (c) Maikap, G. C.; Reddy, M. M.; Mukhopadhyay, M.; Bhatia, B.; Iqbal, J. Tetrahedron 1994, 50, 9145.
80. (d) Bhatia, B.; Reddy, M. M.; Iqbal, J. Tetrahedron Lett. 1993, 34, 6301.
81. Rhenium: (a) He, Y.-X.; Batchelor, R. J.; Einstein, F. W. B.; Peterson, L. K.; Sutton, D. J. Organomet. Chem. 1997, 531, 27.
82. (b) Legoupy, S.; Crévisky, C.; Guillemin, J.-C.; Grée, R. Organometallics 1997, 16, 1822.
83. (c) He, Y.-X.; Batchelor, R. J.; Einstein, F. W. B.; Sutton, D. J. Organomet. Chem. 1996, 509, 37.
84. (d) Batchelor, R. J.; Einstein, F. W. B.; He, Y.-X.; Sutton, D. J. Organomet. Chem. 1994, 468, 183.
85. (e) Casey, C. S.; Yi, C. S. Organometallics 1990, 9, 2413.
86. (a) Pearson, A. J. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 4, p 663.
87. (b) Semmelhack, M. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p 517.
88. (c) Pike, R. D.; Sweigart, D. A. Synlett 1990, 565.
89. (d) Blystone, S. C. Chem. Rev. 1989, 89, 1663.
90. (d) Consiglio, G.; Waymouth, R. W. Chem. Rev. 1989, 89, 257.
91. (e) Pearson, A. J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: Chichester, 1987; Vol. 4, p 889.
92. (a) Stephenson, G. R. In Advanced Asymmetric Synthesis; Stephenson G. R., Ed.; Chapman & Hall: London, U.K., 1996; 313.
93. (b) Alexander, R. P.; Morley, C.; Stephenson, G. R. J. Chem. Soc., Perkin Trans. 1 1988, 2069.
94. (c) Stephenson, G. R.; Alexander, R. P.; Morley, C.; Howard, P. W. Philos. Trans. R. Soc. London 1988, A326, 545.
95. Selected monographs and reviews about organoiron chemistry: (a) Pearson, A. J. Iron Compounds in Organic Synthesis; Academic Press: San Diego, 1994.
96. (b) Pauson, P. L. In Chemistry of Iron; Silver, J., Ed.; Chapman & Hall: Glasgow, U.K., 1993; p 73.
97. (c) Pearson, A. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 663.
98. (d) Fatiadi, A. J. J. Res. Natl. Inst. Stand. Technol. 1991, 96, 1.
99. (e) Astruc, D. In The Chemistry of the Carbon-Metal Bond; Hartley, F. R., Patai, S., Eds.; Wiley: Chichester, 1987; p 625.
100. (f) Eisenorganische Verbindungen in Gmelins Handbuch der Anorganischen Chemie, 8th ed.; B5; Springer: Berlin, 1978; p 97.
101. (g) Togni, A. Hayashi, T. Ferrocenes: Homogeneous Catalysis/Organic Synthesis/Materials Science; Wiley-VCH: Weinheim, 1995.
102. (h) Donaldson, W. A. Aldrich Chim. Acta 1997, 30, 17.
103. (i) Grée, R. Lellouche, J.-P. In Advances of Metal-Organic Chemistry; Liebeskind, L. S., Ed.; Jai Press: Greenwich, Connecticut, 1995; Vol. 4, p 129.
104. Use of π-allyl iron complexes in organic synthesis: (a) Impasto, F. J.; Ihrman, K. G. Helv. Chim. Acta 1961, 83, 3726.
105. (b) Murdoch, H. D.; Weiss, E. Helv. Chim. Acta 1962, 45, 1156.
106. (c) Emmerson, G. F.; Pettit, R. J. Am. Chem. Soc. 1962, 84, 4591.
107. (d) Heck, R. F.; Boss, C. H. J. Am. Chem. Soc. 1964, 86, 2580.
108. (e) Ben-Shoshan, R.; Pettit, R. J. Am. Chem. Soc. 1967, 89, 2231.
109. (f) Nesmeyanov, A. N.; Ustynyk, Y. A.; Kritskaya, I. I.; Shchembelov, G. A. J. Organomet. Chem. 1968, 14, 395.
110. (g) Nesmeyanov, A. N.; Kritskaya, I. I. J. Organomet. Chem. 1968, 14, 387.
111. (h) Young, D. A. T.; Holmes, J. R.; Kaesz, H. D. J. Am. Chem. Soc. 1969, 91, 6968.
112. (i) Gibson, D. H.; Vonnahme, R. L.; Kiernan, J. E. J. Chem. Soc., Chem. Commun. 1971, 720.
113. (j) Whitesides, T. H.; Arhart, R. W. J. Am. Chem. Soc. 1971, 93, 5296.
114. (k) Gibson, D. H.; Vonnahme, R. L. J. Am. Chem. Soc. 1972, 94, 5090.
115. (l) Whitesides, T. H.; Arhart, R. W.; Slawen, R. W. J. Am. Chem. Soc. 1973, 95, 5792.
116. (m) Gibson, D. H.; Vonnahme, R. L. J. Organomet. Chem. 1974, 70, C33.
117. (n) Whitesides, T. H.; Arhart, R. W. Inorg. Chem. 1975, 14, 209.
118. (o) Pearson, A. J. Tetrahedron Lett. 1975, 3617.
119. (p) Brookhart, M.; Whitesides, T. H.; Crocket, J. M. Inorg. Chem. 1976, 15, 1550.
120. (q) Eisenorganische Verbindungen in Gmelins Handbuch der Anorganischen Chemie, 8th ed.; B5, Springer: Berlin, 1978; p 97.
121. (r) Dieter, J.; Nicholas, K. M. J. Organomet. Chem. 1981, 212, 107.
122. (s) Salzer, A.; Hafner, A. Helv. Chim. Acta 1983, 66, 1774.
123. (t) Hafner, A.; von Philipsborn, W.; Salzer, A. Helv. Chim. Acta 1986, 69, 1757.
124. (u) Dieter, J. W.; Li, Z.; Nicholas, K. M. Tetrahedron Lett. 1987, 28, 5415.
125. (v) Li, Z.; Nicholas, K. M. J. Organomet. Chem. 1991, 402, 105.
126. (w) Yeh, M.-C.; Tau, S.-I. J. Chem. Soc., Chem. Commun. 1992, 13.
127. (x) Kuonen, A. M.; Raemy, J.; Jenny, T. A. Chimica 1994, 48, 363.
128. (a) Enders, D.; Fey, P.; Schmitz, T.; Lohray, B. B.; Jandeleit, B. J. Organomet. Chem. 1996, 514, 227.
129. (b) Enders, D.; Frank, U.; Fey, P.; Jandeleit, B.; Lohray, B. B. J. Organomet. Chem. 1996, 519, 147.
130. (c) Enders, D.; von Berg, S.; Jandeleit, B. Synlett 1996, 18.
131. (d) Enders, D.; Jandeleit, B. Liebigs. Ann. Chem. 1995, 1173.
132. (e) Enders, D. Jandeleit, B.; Prokopenko, O. P. Tetrahedron 1995, 51, 6273.
133. (f) Enders, D.; Jandeleit, B. Synthesis 1994, 1327.
134. (g) Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem. 1994, 106, 2033
135. Enders, D.; Jandeleit, B.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1949.
136. (h) Enders, D.; Finkam, M. Synlett 1993, 401.
137. (i) Enders, D.; Finkam, M. Liebigs Ann. Chem. 1993, 551.
138. (j) Schmitz, T. Dissertation, University of Technology Aachen, 1990.
139. (k) Frank, U. Dissertation, University of Technology Aachen, 1990.
140. (l) Fey, P. Dissertation, University of Bonn, 1985.
141. (a) Charlton, M. A.; Green J. R. Can. J. Chem. 1997, 75, 965.
142. (b) Zhou, T.; Green, J. R. Tetrahedron Lett. 1993, 34, 4497.
143. (c) Gadja, C.; Green, J. R. Synlett 1992, 973.
144. (d) Green, J. R.; Carrol, M. K. Tetrahedron Lett. 1991, 32, 1141.
145. (a) de Koning, H.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N. Eur. J. Org. Chem. 1998, 1729.
146. (b) Speckamp, W. N. Pure Appl. Chem. 1996, 68, 695.
147. (c) Goubitz, G.; Seljée, F. R.; Schenk, H.; Hopman, J. C. P.; Hiemstra, H. Z. Kristallogr. 1996, 211, 714.
148. (d) Goubitz, G.; Seljée, F. R.; Koot, W.-J.; Hiemstra, H. Z. Kristallogr. 1996, 211, 711.
149. (e) Koot, W.-J. Dissertation, University of Amsterdam, 1993.
150. (f) Hofpman, J. C. P.; Hiemstra, H.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1995, 617.
151. (g) Hopman, J. C. P.; Hiemstra, H.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1995, 619.
152. (h) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Chem. Soc., Chem. Commun. 1993, 156.
153. Jackson, R. W. F.; Turner, D.; Block, M. J. Synlett 1997, 789.
154. (a) Nakanishi, S.; Okamoto, K.; Yamagushi, H.; Takata, T. Synthesis 1998, 1735.
155. (b) Nakanishi, S.; Memita, S.; Takata, T.; Itoh, K. Bull. Chem. Soc. Jpn. 1998, 71, 403.
156. (c) Yamaguchi, H.; Nakanishi, S.; Takata, T. J. Organomet. Chem. 1998, 554, 167.
157. (d) Yamaguchi, H.; Nakanishi, S.; Okamoto, K.; Takata, T. Synlett 1997, 722.
158. (e) Nakanishi, S.; Takata, T. Rev. Heteroat. Chem. 1997, 17, 153.
159. (f) Nakanishi, S.; Yamaguchi, H.; Okamoto, K.; Takata, T. Tetrahedron: Asymmetry 1996, 7, 2219.
160. (g) Itoh, K.; Otsuji, Y.; Nakanishi, S. Tetrahedron Lett. 1995, 36, 5211.
161. (a) Ley, S. V.; Cox, L. R.; Middleton, B.; Worrall, J. M. Tetrahedron 1999, 55, 3515.
162. (b) Cox, L. R.; Ley, S. V. Chem. Soc. Rev. 1998, 27, 301.
163. (c) Ley, S. V.; Cox, L. R.; Worrall, J. M. J. Chem. Soc., Perkin Trans. 1 1998, 3349.
164. (d) Ley, S. V.; Middleton, B. Chem. Commun. 1998, 1995.
165. (e) Cox, L. R.; Ley, S. V. J. Chem. Soc., Chem. Commun. 1998, 1339.
166. (f) Ley, S. V.; Burckhardt, S.; Cox, L. R.; Worrall, J. M. J. Chem. Soc., Chem. Commun. 1998, 229.
167. (g) Ley, S. V.; Cox, L. R. J. Chem. Soc., Chem. Commun. 1998, 227.
168. (h) Ley, S. V.; Cox, L. R.; Meek, G. Chem. Rev. 1996, 96, 423.
169. (a) Enders, D.; Jandeleit, B.; von Berg, S. In Organic Synthesis via Organometallics, OSM V; Helmchen, G., Dibo, J., Flubacher, D., Wiese, B., Eds.; Vieweg: Braunschweig, 1997; p 279.
170. (b) Enders, D.; Jandeleit, B.; von Berg, S. Synlett 1997, 421.
171. Review about chemical processes involving self-reproduction of chirality: Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem. 1996, 108, 2280
172. Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708.
173. Recent examples of applications of palladium metal catalysis in chirality transfer reactions: (a) Doi, T, Yanagisawa, M, Miyazawa, Yamamoto, K., Tetrahedron: Asymmetry 1995, 6, 389.
174. (b) Suginome, M.; Iwanami, T.; Matsumoto, A.; Ito, Y. Tetrahedron: Asymmetry 1997, 8, 859.
175. (c) Michelet, V.; Genêt, J.-P. Bull. Soc. Chim. Fr. 1996, 133, 881. For other transition metal catalyzed chirality transfer reactions, see for example ref 6-8, 14.
176. Seebach, D. Angew. Chem. 1979, 91, 259
177. Seebach, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 239.
178. (b) Hase, T. A. Umpoled Synthons; John Wiley & Sons: New York, 1987.
179. Enders, D.; Jandeleit, B.; Raabe, G. University of Technology Aachen, 1995, unpublished results.
180. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999.
181. (b) Ito, Y.; Kobayshi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767.
182. (c) Banfi, L.; Bernardi, A.; Colombo, L.; Gennari, C.; Scolastico, C. J. Org. Chem. 1984, 49, 3784.
183. (d) Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
184. Enders, D.; Klatt, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed., John Wiley & Sons: New York, 1995; Vol. 1, p 178.
185. (a) Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, M. P.; Masamune, S.; Roush, W. R. Tetrahedron Lett. 1984, 25, 2183.
186. (b) Rathke, M. W.; Novak, M. J. Org. Chem. 1985, 50, 2624.
187. (c) Enders, D.; von Berg, S.; Jandeleit, B. Org. Synth. 2001, 78, 177.
188. (a) Shahak, I.; Almog. Synthesis 1969, 170.
189. (b) Shahak, I.; Almog. Synthesis 1970, 145.
190. (c) Plee, J. W.; Oh, D. Y. Synth. Commun. 1990, 20, 273.
191. (d) Lee, J. W.; Oh, D. Y. Synth. Commun. 1989, 19, 2209.
192. (e) Enders, D.; von Berg, S.; Jandeleit, B. Org. Synth. 2001, 78, 169.
193. Lombardo, L.; Taylor, R. J. K. Synthesis 1978, 131.
194. Alkene (S)-8 is commercially avaliable from ACROS Chimica, Belgium. Enders, D.; Jandeleit, B. ACROS Org. Acta 1995, 1, 59.
195. (a) Hanessian, S.; Lavelee, P. Can. J. Chem. 1977, 55, 562.
196. (b) Hanessian, S.; Lavelee, P. Can. J. Chem. 1975, 53, 2975.
197. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem. 1978, 90, 602
198. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569.
199. Clinton, N. A.; Lillya, C. P. J. Am. Chem. Soc. 1970, 92, 3058.
200. Braye, E. H.; Hübel, W. Inorg. Synth. 1966, 8, 179.
201. (a) Enders, D.; Jandeleit, B. von Berg, S. Org. Synth. 2001, 78, 189.
202. Enders, D.; Schmitz, T.; Raabe, G.; Krüger, C. Acta Crystallogr. 1991, C47, 37.
203. Helmchen, G. In Methods of Organic Chemistry; Houben-Weyl, 1995; Vol. E, p 21a.
204. (b) Prelog, V.; Helmchen, G. Angew. Chem. 1982, 94, 614
205. Prelog, V.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1982, 21, 567.
206. (c) Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem. 1966, 78, 413.
207. (a) Guilard, R.; Dusalisoy, Y. J. Organomet. Chem. 1979, 77, 393.
208. (b) McCaskie, J. E.; Chang, P. L.; Nelson, T. R.; Dittmer, D. C. J. Org. Chem. 1973, 38, 3963.
209. (c) Nesmeyanov, A. N.; Rybin, L. V.; Rybinskaya, M. I.; Gubenko, N. T., Leshcheva, I. F.; Ustynyuk, Y. A. J. Gen. Chem. USSR (Engl. Transl.) 1968, 38, 1428.
210. (d) Ibbotson, A.; Reduto dos Reis, A. C.; Saberi, S. P.; Slawin, A. M. Z.; Thomas, S. E.; Tustin, G. J.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1992, 1251.
211. -3. Further details of the crystal structure investigation may be obtained from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopold-shafen (FRG), on quoting the depository number CSD-58339.
212. (a) Sheldrick, G. M. SHELXS-86; University of Göttingen, 1986.
213. (b) Hall, S. R.; Flack, H. D.; Stewart, J. M. Xtal3.2 Reference Manual; Universities of Western Australia (Perth), Geneva, Maryland; Lamb: Perth, 1992.
214. Keller, E. SCHAKAL 86; University of Freiburg, 1986.
215. (a) Cano, A. C.; Zúñiga-Villarreal, N.; Alvarez, C.; Toscano, T. R. A.; Cervantes, M.; Diaz, A.; Rudler, H. J. Organomet. Chem. 1994, 464, C23.
216. (b) Chow, T. J.; Hwang, J.-J.; Wen, Y.-S.; Lin, S.-C. J. Chem. Soc., Dalton Trans. 1994, 937.
217. (c) Rybin, L. V.; Rybinskaya, M. I. Russ. Chem. Rev. 1993, 62, 637.
218. (d) Liu, L.-K.; Sun, C.H.; Yang, C.-Z.; Wen, Y.-S.; Wu, C.-F.; Shih, S.-Y.; Lin, K.-S. Organometallics 1992, 11, 972.
219. (e) Hsiou, Y.; Wang, Y.; Liu, L.-K. Acta Crystallogr. 1989, 45, 721.
220. (f) Lei, P.-S.; Vogel, P. Acta Crystallogr. 1986, 5, 2500.
221. (f) Whitesides, T. H.; Slawen, R. W.; Calabrese, J. C. Inorg. Chem. 1974, 13, 1895.
222. (g) Luxmoore, A. R.; Truter, M. R. Acta Crystallogr. 1962, 15, 1117.
223. Lin, S.-H.; Chen, C.-C.; Vong, W.-J.; Liu, R.-S. Organometallics 1995, 14, 1619.
224. 3-allyl)dicarbonyl[hydrotris(1-pyrazolyl)-borato]molybdenum complex see: Ward, Y. D.; Villanueva, L. A.; Allred, G. D.; Payne, S. C.; Semones, M. A.; Liebeskind, L. S. Organometallics 1995, 14, 4132.
225. Enyl complexes are by definition those that contain discrete σ- and π-metal carbon interactions within a single ligand. Sharp, P. R. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Chapter 2, p 272. Enyl complexes are discussed as intermediates for example in Rh-, Ir-, and Fe-catalyzed allylic substitutions with chirality transfer. See refs 7, 8, 14
226. Alkene rac-6f was synthesized according to refs 34, 35 and obtained in 83% isolated yield from racemic 2-acetoxypropanal (gift from BASF AG) and the phenylsulfonyl-substituted phosphonate 5.
227. 3-allyl)tricarbonyl(1-) complex: Chang, S.; Yoon, J.; Brookhart, M, J. Am. Chem. Soc. 1994, 116, 1869.
228. Akermark, B.; Krakenberger, B.; Hansson, S. Organometallics 1987, 6, 620.
229. (a) Bonafoux, D.; Bordeau, M.; Biran, C.; Cazeau, P.; Dunogues, J. J. Org. Chem. 1996, 61, 5532.
230. (b) Emde, H.; Götz, A.; Hofmann, K.; Simchen, G. Liebigs Ann. Chem. 1981, 1643.
231. (d) Revis, A.; Hilty, T. K. J. Org. Chem. 1990, 55, 2972.
232. (e) Ainsworth, C.; Chen, F.; Kuo, Y.-N. J. Organomet. Chem. 1972, 46, 59.
233. (a) Burka, L. T.; Iles, J. Phytochemistry 1979, 18, 873.
234. (b) Burka, L. T.; Kahnert, L.; Wilson, B. J.; Harris, T. M. J. Am. Chem. Soc. 1977, 99, 2302.
235. (c) Oba, K.; Uritani, I. Plant Cell Physiol. 1979, 20, 819.
236. Enders, D; Jandeleit, B.; von Berg, S. J. Organomet. Chem. 1997, 533, 219.
237. Enders, D.; Jandeleit, B. University of Technology Aachen, 1995, unpublished results.
238. (a) Wessel, H.-P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin Trans. 1 1985, 2247.
239. (b) Iversen, T.; Bundle, D. R. J. Chem. Soc., Chem. Commun. 1981, 1240.
240. (c) Ainsworth, C.; Chen, F.; Kuo, Y.-N. J. Organomet. Chem. 1972, 46, 59.