Synthesis and characterization of new biphenolate and binaphtholate rare-earth-metal amido complexes: Catalysts for asymmetric olefin hydroamination/cyclization

Chemistry - A European Journal

Volumn 9, Issue 19, 2003, Pages 4796-4810

  Gribkov, Denis V ^a   Hultzsch, Kai C ^a   Hampel, Frank ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Assymetric catalysis; Hydroamination; Lanthanum; O ligands; Rare earth compounds; Yttrium

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; COMPLEXATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

HETEROCHIRAL COMPLEXES;

CATALYSTS;

ALKENE; AMIDE; LANTHANIDE; NAPHTHOL DERIVATIVE; PHENOL DERIVATIVE; PYRROLIDINE DERIVATIVE; SILICON DERIVATIVE; YTTRIUM;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHIRALITY; COMPLEX FORMATION; CYCLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HEATING; HYDROAMINATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 0142056080     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304975     Document Type: Article

References (191)

1. For general and comprehensive reviews on this topic see: a) R. Taube in Applied Homogeneous Catalysis, Vol. 1 (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 1996, pp. 507-520;
2. b) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675-703;
3. c) M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105-4108; Angew. Chem. Int. Ed. 2001, 40, 3983-3985;
4. c) M. Nobis, B. Drießen-Hölscher, Angew. Chem. 2001, 113, 4105-4108; Angew. Chem. Int. Ed. 2001, 40, 3983-3985;
5. d) J. J. Brunet, D. Neibecker in Catalytic Heterofunctionalization from Hydroamination to Hydrozirconation; (Eds.: A. Togni, H. Grützmacher), Wiley-VCH, Weinheim, 2001, pp. 91-141;
6. e) J. Seayad, A. Tillack, C. G. Hartung, M. Beller Adv. Synth. Catal. 2002, 344, 795-813;
7. f) M. Beller, C. Breindl, M. Eichberger, C. G. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 1579-1594;
8. g) F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104-114.
9. For hydroamination of alkynes with group IV metal catalysts see: a) P. J. Walsh, A. M. Baranger, R. G. Bergman, J. Am. Chem. Soc. 1992, 114, 1708-1719;
10. b) A. M. Baranger, P. J. Walsh, R. G. Bergman, J. Am. Chem. Soc. 1993, 115, 2753-2763;
11. c) P. L. McGrane, M. Jensen, T. Livinghouse, J. Am. Chem. Soc. 1992, 114, 5459-5460;
12. d) P. L. McGrane, T. Livinghouse, J. Am. Chem. Soc. 1993, 115, 11485-11489;
13. e) E. Haak, I. Bytschkov, S. Doye, Angew. Chem. 1999, 111, 3584-3586; Angew. Chem. Int. Ed. 1999, 38, 3389-3391;
14. e) E. Haak, I. Bytschkov, S. Doye, Angew. Chem. 1999, 111, 3584-3586; Angew. Chem. Int. Ed. 1999, 38, 3389-3391;
15. f) E. Haak, H. Siebeneicher, S. Doye, Org. Lett. 2000, 2, 1935-1938;
16. g) J. S. Johnson, R. G. Bergman, J. Am. Chem. Soc. 2001, 123, 2923-2924;
17. h) Y. Shi, J. T. Ciszewski, A. L. Odom, Organometallics 2001, 20, 3967-3969;
18. i) C. Cao, J. T. Ciszewski, A. L. Odom, Organometallics 2001, 20, 5011-5013;
19. j) Bytschkov, S. Doye, Eur. J. Org. Chem. 2001, 4411-4418;
20. k) B. F. Straub, R. G. Bergman, Angew. Chem. 2001, 113, 4768-4771; Angew. Chem. Int. Ed. 2001, 40, 4632-4635;
21. k) B. F. Straub, R. G. Bergman, Angew. Chem. 2001, 113, 4768-4771; Angew. Chem. Int. Ed. 2001, 40, 4632-4635;
22. l) T.-G. Ong, G. P. A. Yap, D. S. Richeson, Organometallics 2002, 21, 2839-2841;
23. m) A. Heutling, S. Doye, J. Org. Chem. 2002, 67, 1961-1964;
24. n) E. Haak, I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2002, 457-463;
25. o) H. Siebeneicher, S. Doye, Eur. J. Org. Chem. 2002, 1213-1220;
26. p) L. Ackermann, R. G. Bergman, Org. Lett. 2002, 4, 1475-1478;
27. q) C. Cao, Y. Shi, A. L. Odom, Org. Lett. 2002, 4, 2853-2856;
28. r) A. Tillack, I. G. Castro, C. G. Hartung, M. Beller, Angew. Chem. 2002, 114, 2646-2648; Angew. Chem. Int. Ed. 2002, 41, 2541-2543;
29. r) A. Tillack, I. G. Castro, C. G. Hartung, M. Beller, Angew. Chem. 2002, 114, 2646-2648; Angew. Chem. Int. Ed. 2002, 41, 2541-2543;
30. s) I. Bytschkov, S. Doye, Tedrahedron Lett. 2002, 43, 3715-3718;
31. t) Y. Shi, C. Hall, J. T. Ciszewski, C. Cao, A. L. Odom, Chem. Commun. 2003, 586-587.
32. For hydroamination of alkynes with actinide catalysts see: a) A. Haskel, T. Straub, M. S. Eisen, Organometallics 1996, 15, 3773-3775;
33. b) T. Straub, A. Haskel, T. G. Neyroud, M. Kapon, M. Botoshansky, M. S. Eisen, Organometallics 2001, 20, 5017-5035;
34. c) J. Wang, A. K. Dash, M. Kapon, J.-C. Berthet, M. Ephritikhine, M. S. Eisen, Chem. Eur. J. 2002, 8, 5384-5396.
35. For hydroamination of activated olefins with anilines by using late transition metal catalysts see: a) A. L. Casalnuovo, J. C. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738-6744;
36. b) J.-J. Brunet, D. Neibecker, K. Philippot, Tedrahedron Lett. 1993, 34, 3877-3880;
37. c) J.-J. Brunet, G. Commenges, D. Neibecker, K. Philippot, J. Organomet. Chem. 1994, 469, 221-228;
38. d) R. Dorta, P. Egli, F. Zürcher, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857-10858;
39. e) M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 9546-9547;
40. f) O. Löber, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 4366-4367;
41. g) U. Nettekoven, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 1166-1167;
42. h) M. Tokunaga, M. Eckert, Y. Wakatsuki, Y. Angew. Chem. 1999, 111, 3416-3419; Angew. Chem. Int. Ed. 1999, 38, 3222-3225;
43. h) M. Tokunaga, M. Eckert, Y. Wakatsuki, Y. Angew. Chem. 1999, 111, 3416-3419; Angew. Chem. Int. Ed. 1999, 38, 3222-3225;
44. i) Beller, H. Trauthwein, M. Eichberger, C. Breindl, T. E. Müller, Eur. J. Inorg. Chem. 1999, 1121-1132;
45. j) T. Minami, H. Okamoto, S. Ikeda, R. Tanaka, F. Ozawa, M. Yoshifuji, Angew. Chem. 2001, 113, 4633-4635; Angew. Chem. Int. Ed. 2001, 40, 4501-4503;
46. j) T. Minami, H. Okamoto, S. Ikeda, R. Tanaka, F. Ozawa, M. Yoshifuji, Angew. Chem. 2001, 113, 4633-4635; Angew. Chem. Int. Ed. 2001, 40, 4501-4503;
47. k) M. Kawatsura, J. F. Hartwig, Organometallics 2001, 20, 1960-1964;
48. l) C. G. Hartung, A. Tillack, H. Trauthwein, M. Beller, J. Org. Chem. 2001, 66, 6339-6343.
49. a) M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992,114, 275-294;
50. b) M. R. Gagné, L. Brard, V. P. Conticello, M. A. Giardello, T.J. Marks, C.L. Stern, Organometallics 1992, 11, 2003-2005;
51. c) M. A. Giardello, V. P. Conticello, L. Brard, M. Gagné, T. J. Marks, J. Am. Chem. Soc. 1994; 116, 10241-10254;
52. d) M. R. Douglass, M. Ogasawara, S. Hong, M. V. Metz, T. J. Marks, Organometallics 2002, 21, 283-292;
53. e) S. Hong, T. J. Marks, J. Am. Chem. Soc. 2002, 124, 7886-7887;
54. f) Y. Li, P.-F. Fu, T. J. Marks, Organometallics 1994, 13, 439-440;
55. g) Y. Li, T. J. Marks, Organometallics 1996, 15, 3770-3772;
56. h) Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996,118, 9295-9306;
57. i) Y. Li, T.J. Marks, J. Am. Chem. Soc. 1998, 120, 1757-1771;
58. j) V. M. Arredondo, F. E. McDonald, T. J. Marks, J. Am. Chem. Soc. 1998, 120, 4871-4872;
59. k) A. T. Gilbert, B. L. Davis, T. J. Emge, R. D. Broene, Organometallics 1999, 18, 2125-2132;
60. l) V. M. Arredondo, S. Tian, F. E. McDonald, T. J. Marks,J. Am. Chem. Soc. 1999, 121, 3633-3639;
61. m) G. A. Molander, E. D. Dowdy, J. Org. Chem. 1999, 64, 6515-6517;
62. n) V. M. Arredondo, F. E. McDonald, T J. Marks, Organometallics 1999, 18, 1949-1960;
63. o) G. A. Molander, E. D. Dowdy, S. K. Pack, J. Org. Chem. 2001, 66, 4344-4347;
64. p) J.-S. Ryu, T. J. Marks, F. E. McDonald, Org. Lett. 2001, 3, 3091-3094.
65. a) M. R. Bürgstein, H. Berberich, P. W. Roesky, Organometallics 1998, 17, 1452-1454;
66. b) Y. K. Kim, T. Livinghouse, J. E. Bercaw, Tedrahedron Lett. 2001, 42, 2933-2935;
67. c) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797-3799; Angew. Chem. Int. Ed. 2002, 41, 3645-3647.
68. c) Y. K. Kim, T. Livinghouse, Angew. Chem. 2002, 114, 3797-3799; Angew. Chem. Int. Ed. 2002, 41, 3645-3647.
69. For an overview of applications of rare earth metals as reagents or catalysts in organic synthesis and polymerization catalysis see: a) G. A. Molander, Chem. Rev. 1992, 92, 29-68;
70. b) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307-338;
71. c) F. T. Edelmann, Top. Curr. Chem. 1996, 179, 247-276;
72. d) H. Yasuda, Top. Organomet. Chem. 1999, 2, 255-283;
73. e) H. C. Aspinall, Chem. Rev. 2002, 102, 1807-1850;
74. f) G. A. Molander, J. A. C. Romero, Chem. Rev. 2002, 102, 2161-2185;
75. g) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187-2210;
76. h) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.-L. Lam, Chem. Rev. 2002, 102, 2227-2302;
77. i) K. Mikami, M. Terada, H. Matsuzawa, Angew. Chem. 2002, 114, 3704-3722; Angew. Chem. Int. Ed. 2002, 41, 3554-3571;
78. i) K. Mikami, M. Terada, H. Matsuzawa, Angew. Chem. 2002, 114, 3704-3722; Angew. Chem. Int. Ed. 2002, 41, 3554-3571;
79. j) Z. Hou, Y. Wakatsuki, Coord. Chem. Rev. 2002, 231-22.
80. Epimerization of planar chiral cyclopentadienyl complexes is quite a general phenomenon in rare-earth-metal chemistry, see: a) M. A. Giardello, V. P. Conticello, L. Brard, M. Sabat, A. L. Rheingold, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10212-10240;
81. b) C. M. Haar, C. L. Stern, T. J. Marks, Organometalics 1996, 15, 1765-1784;
82. c) K. C. Hultzsch, T. P. Spaniol, J. Okuda, Organometallics 1997, 16, 4845-4856;
83. d) J. C. Yoder, M. W. Day, J. E. Bercaw, Organometallics 1998, 17, 4946-4958;
84. e) J. Eppinger, Ph.D. thesis, Technische Universität München (Germany), 1999.
85. C. J. Schaverien, N. Meijboom, A. G. Orpen, J. Chem. Soc. Chem. Commun. 1992, 124-126.
86. a) A. H. Hoveyda, R. R. Schrock, Chem. Eur. J. 2001, 7, 945-950;
87. b) J. B. Alexander, D. S. La, D. R. Cefalo, A. H. Hoveyda, R. R. Schrock, J. Am. Chem. Soc. 1998, 120, 4041-4042;
88. c) J. B. Alexander, R. R. Schrock, W. M. Davis, K. C. Hultzsch, A. H. Hoveyda, J. H. Houser, Organometallics 2000, 19, 3700-3715;
89. d) S. S. Zhu, D. R. Cefalo, D. S. La, J. Y. Jamieson, W. M. Davis, A. H. Hoveyda, R. R. Schrock, J. Am. Chem. Soc. 1999, 121, 8251-8259;
90. e) W. C. Tsang, R. R. Schrock, A. H. Hoveyda, Organometallics 2001, 20, 5658-5669.
91. 2(Biphen) is commercially available from Strem Chemicals, Inc. in enantiopure form. Enantiopure binaphthol is available for a price of ca. 800 ε per kg from Reuter Chemische Apparatebau KG (RCA), Freiburg, Germany.
92. D. C. Bradley, J. S. Ghotra, F. A. Hart, J. Chem. Soc. Dalton Trans. 1973, 1021-1023.
93. Additionally, all attempts to prepare biphenolate or binaphtholate complexes of any of the ligands discussed here by salt metathesis have failed so far.
94. Ligands given without configuration are racemates.
95. R. Anwander, O. Runte, J. Eppinger, G. Gerstberger, E. Herdtweck, M. Spiegler, J. Chem. Soc. Dalton Trans. 1998, 847-858.
96. 2], see: T. I. Gountchev, T. D. Tilley, Organometallics 1999, 18, 5661-5667.
97. R. D. Shannon, Acta Crystallogr. 1976, A32, 751-767.
98. 2 has been proven by single-crystal X-ray diffraction: D. V. Gribkov, F. Hampel, K. C. Hultzsch, unpublished results;
99. b) However, (R,S)-3a dissociates to 2a to a small extent (10 %) upon heating to 100°C.
100. a) D. S. Lingenfelter, R. C. Helgeson, D. J. Cram, J. Org. Chem. 1981, 46, 393-406;
101. b) P. Wipf, J.-K. Jung, J. Org. Chem. 2000, 65, 6319-6337.
102. a) P. J. Cox, W. Wang, V. Snieckus, Tedrahedron Lett. 1992, 33 2253-2256;
103. b) K. Maruoka, N. Murase, H. Yamamoto, J. Org. Chem. 1993, 58, 2938-2939;
104. c) K. Ishihara, H. Yamamoto,J. Am. Chem. Soc. 1994, 116, 1561-1562;
105. d) W.-S. Huang, Q.-S. Hu, L. Pu, J. Org. Chem. 1998, 63, 1364-1365;
106. e) K. B. Simonsen, K. V. Gothelf, K. A. Jorgensen, J. Org. Chem. 1998, 63, 7536-7538;
107. f) P. Kratky, U. Haslinger, M. Widhalm, Monatsh. Chem. 1998, 129, 1319-1327.
108. P. L. Arnold, L. S. Natrajan, J. J. Hall, S. J. Bird, C. Wilson, J. Organomet. Chem. 2002, 647, 205-215.
109. a) T. J. Boyle, D. L. Barnes, J. A. Heppert, L. Morales, F. Takusagawa, J. W. Connolly, Organometallics 1992, 11, 1112-1126;
110. b) T. J. Boyle, N. W. Eilerts, J. A. Heppert, E Takusagawa, Organometallics 1994, 13, 2218-2229;
111. c) E. J. Corey, M. A. Letavic, M. C. Noe, S. Sarshar, Tedrahedron Lett. 1994, 35, 7553-7556;
112. d) T. Arai, H. Sasai, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 441-442;
113. e) M. Terada, Y. Matsumoto, Y. Nakamura, K. Mikami, Inorg. Chim. Acta 1999, 296, 267-272;
114. f) T. Davis, J. Balsells, P. J. Carroll, P. J. Walsh, Org. Lett. 2001, 3, 699-702;
115. g) H. Nöth, A. Schlegel, M. Suter, J. Organomet. Chem. 2001, 621, 231-241;
116. h) S. Chitsaz, B. Neumüller, Organometallics 2001, 20, 2338-2343;
117. i) A. Kayal, S. C. Lee, Inorg. Chem. 2001, 41, 321-330.
118. a) A. Kayal, A. F. Ducruet, S. C. Lee, Inorg. Chem. 2000, 40, 3696-3704;
119. b) H. C. Aspinall, J. M. Bickley, J. L. M. Dwyer, N. Greeves, A. Steiner, Angew. Chem. 2000, 112, 2980-2983; Angew. Chem. Int. Ed. 2000, 39, 2858-2861.
120. b) H. C. Aspinall, J. M. Bickley, J. L. M. Dwyer, N. Greeves, A. Steiner, Angew. Chem. 2000, 112, 2980-2983; Angew. Chem. Int. Ed. 2000, 39, 2858-2861.
121. a) W. J. Evans, J. M. Olofson, J. W. Ziller, Inorg. Chem. 1989, 28, 4308-4309, references therein;
122. b) M. H. Chisholm, Polyhedron 1983, 2, 681-721;
123. c) R. C. Mehrotra, A. Singh, U. M. Tripathi, Chem. Rev. 1991, 91, 1287-1303;
124. d) R. Anwander, Top. Curr. Chem. 1996, 179, 149-245.
125. See for example: a) P. B. Hitchcock, M. F. Lappert, R. G. Smith, Inorg. Chim. Acta 1987, 139, 183-184;
126. b) H. Schumann, J. Winterfeld, R. D. Kohn, L. Esser, J. Sun, A. Dietrich, Chem. Ber. 1993, 126, 907-912;
127. c) G. B. Deacon, B. M. Gatehouse, Q. Shen, G. N. Ward, E. R. T. Tiekink, Polyhedron 1993, 12, 1289-1294;
128. d) R. J. Butcher, D. L. Clark, S. K. Grumbine, R. L. Vincent-Hollis, B. L. Scott, J. G. Watkin, Inorg. Chem. 1995, 34, 5468-5476;
129. e) D. L. Clark, G. B. Deacon, T. Feng, R. V Hollis, B. L. Scott, B. W. Skelton, J. G. Watkin, A. H. White, Chem. Commun. 1996, 1729-1730;
130. f) D. L. Clark, R. V. Hollis, B. L. Scott, J. G. Watkin, Inorg. Chem. 1996, 35, 667-674;
131. g) W. J. Evans, M. Ansari, J. W. Ziller, S. I. Khan, J. Organomet. Chem. 1998, 553, 141-148;
132. h) H. C. Aspinall, J. E Bickley, J. L. M. Dwyer, R. V. Kelly, A. Steiner, Organometallics 2000, 19, 5416-5423;
133. i) G. B. Deacon, T. Feng, C. M. Forsyth, A. Gitlits, D. C. R. Hockless, Q. Shen, B. W. Skelton, A. H. White, J. Chem. Soc. Dalton Trans. 2000, 961-966.
134. a) W. J. Evans, T. J. Boyle, J. W. Ziller, Organometallics 1993, 12, 3998-4009;
135. b) R. Anwander, J. Eppinger, I. Nagl, W. Scherer, M. Tafipolsky, P. Sirsch, Inorg. Chem. 2000, 39, 4713-4720;
136. c) C. E. Daitch, P. D. Hampton, E. N. Duesler, T. M. Alam, J. Am. Chem. Soc. 1996, 118, 7769-7773.
137. K. C. Hultzsch, P. Voth, K. Beckerle, T. P. Spaniol, J. Okuda, Organometallics 2000, 19, 228-243, and references therein.
138. 2(μ-O2): La-N = 2.37(2), 2.49(2) Å, see: D. C. Bradley, J. S. Ghotra, E A. Hart, M. B. Hursthouse, P. R. Raithby, J. Chem. Soc. Dalton Trans. 1977, 1166-1172;
139. 2NMe)]: La-N = 2.31(2) Å, see: ref. [5a];
140. 3]: La-N = 2.443(7)-2.469(8) Å, see: J. Guan, S. Jin, Y. Lin, Q. Shen, Organometallics 1992, 11, 2483-2487;
141. 2: La-N = 2.40(1) Å, see: 2.40(1) Å, see: H.C. Aspinall, S.R. Moore, A. K. Smith, J. Chem. Soc. Dalton Trans. 1992, 153-156;
142. 2}Li(thf)]: La-N = 2.30(1) Å, see: H.C. Aspinall, S. R. Moore, A. K. Smith, J. Chem. Soc. Dalton Trans. 1993, 993-996;
143. 2] (1b): La-N = 2.395(5)-2.416(5) Å, see ref. [15];
144. 2}]: La-N = 2.453(4) Å, see: K. Kincaid, C. P. Gerlach, J. R. Hagadom, G. D. Whitener, A. Shafir, J. Arnold, Organometallics 1999, 18, 5360-5366;
145. 2}]: La-N = 2.449(3) Å, see: J. Eppinger, M. Spiegler, W. Hieringer, W. A. Herrmann, R. Anwander, J. Am. Chem. Soc. 2000, 122, 3080-3096;
146. 2: La-N = 2.331(8), 2.352(9) Å, see: J. Collin, N. Giuseppone, N. Jaber, A. Domingos, L. Maria, I. Santos, J. Organomet. Chem. 2001, 628, 271-274;
147. 2 = 2.377(3), 2.382(3) Å, see: G. R. Giesbrecht, G. D. Whitener, J. Arnold, J. Chem. Soc. Dalton Trans. 2001, 923-927;
148. 2}]: La-N = 2.361(5), 2.381(4) Å, see: M. G. Kimpel, H. W. Görlitzer, M. Tafipolsky, M. Spiegler, W. Scherer, R. Anwander, J. Organomet. Chem. 2002, 647, 236-244.
149. 2] (1a): Y-N = 2.229(4)-2.276(4) Å, see: W. A. Herrmann, R. Anwander, F. C. Munck, W. Scherer, V. Dufaud, N. W. Huber, G. R. J. Artus, Z. Naturforsch. 1994, 49B, 1789-1797.
150. a) W. S. Rees, Jr., O. Just, H. Schumann, R. Weimann, Angew. Chem. 1996, 108, 481-483; Angew. Chem. Int. Ed. Engl. 1996, 35, 419-422;
151. a) W. S. Rees, Jr., O. Just, H. Schumann, R. Weimann, Angew. Chem. 1996, 108, 481-483; Angew. Chem. Int. Ed. Engl. 1996, 35, 419-422;
152. b) W. Hieringer, J. Eppinger, R. Anwander, W. A. Herrmann, J. Am. Chem. Soc. 2000, 122, 11983-11994.
153. This is only an approximation based on the equation given by Kagan, see: H. B. Kagan, J. C. Fiaud, Top. Stereochem. 1988, 18, 249-330. However, this calculation is based on a first-order equation that does not take side reactions, e.g. formation of achiral cis products, into account.
154. a) C. J. Schaverien, A. G. Orpen, Inorg. Chem. 1991, 30, 4968-4978;
155. b) L. Lee, D. J. Berg, G. W. Bushnell, Organometallics 1995,14, 8-10;
156. c) Y. Mu, W. E. Piers, D. C. MacQuarrie, M. J. Zaworotko, V. G. Young, Jr., Organometallics 1996, 15, 2720-2726;
157. d) L. Lee, D. J. Berg, F. W. Einstein, R. J. Batchelor, Organometallics 1997, 16, 1819-1821;
158. e) K. C. Hultzsch, T. P. Spaniol, J. Okuda, Angew. Chem. 1999, 111, 163-166; Angew. Chem. Int. Ed. 1999, 38, 227-230;
159. e) K. C. Hultzsch, T. P. Spaniol, J. Okuda, Angew. Chem. 1999, 111, 163-166; Angew. Chem. Int. Ed. 1999, 38, 227-230;
160. f) S. Tian, V. M. Arredondo, C. L. Stern, T. J. Marks, Organometallics 1999, 18, 2568-2570;
161. g) S. Arndt, P. Voth, T. P. Spaniol, J. Okuda, Organometallics 2000, 19, 4690-4700;
162. h) A. A. Trifonov, T. P. Spaniol, J. Okuda, Organometallics 2001, 20, 4869-4874;
163. i) W. J. Evans, J. C. Brady, J. W. Ziller, J. Am. Chem. Soc. 2001, 123, 7711-7712;
164. j) D. J. H. Emslie, W. E. Piers, M. Parvez, R. McDonald, Organometallics 2002, 21, 4226-4240;
165. k) F. Estler, G. Eickerling, E. Herdtweck, R. Anwander, Organometallics 2003, 22, 1212-1222.
166. a) L. Lee, D. J. Berg, G. W. Bushnell, Inorg. Chem. 1994, 33, 5302-5308;
167. b) P. Shao, D. J. Berg, G. W. Bushnell, Inorg. Chem. 1994, 33, 6334-6339;
168. c) Y. Mu, W. E. Piers, M.-A. MacDonald, M. J. Zaworotko, Can. J. Chem. 1995, 73, 2233-2238;
169. d) O. Runtei, T. Priermeier, R. Anwander, J. Chem. Soc. Chem. Commun. 1996, 1385-1386;
170. e) H. W. Görlitzer, M. Spiegler, R. Anwander, Eur. J. Inorg. Chem. 1998, 1009-1014;
171. f) H. W. Görlitzer, M. Spiegler, R. Anwander, J. Chem. Soc. Dalton Trans. 1999, 4287-4288.
172. A. K. Dash, A. Razavi, A. Mortreux, C. W. Lehmann, J.-F. Carpentier, Organometallics 2002, 21, 3238-3249.
173. M. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028-4036.
174. C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2922-2959.
175. C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2922-2959.
176. M. B. Finn, K. B. Sharpless in Asymmetric Synthesis, Vol. 5 (Ed.: J. D. Morrison), Academic Press, New York, 1985, Chapter 8.
177. Y. Tamaru, M. Hojo, H. Higashimura, Z.-I. Yoshida, J. Am. Chem. Soc. 1988, 110, 3994-4002.
178. a) H. O. House, L. F. Lee, J. Org. Chem. 1976, 41, 863-869;
179. b) K. Harding, S. R. Burks, J. Org. Chem. 1981, 46, 3920-3922.
180. This procedure can be easily scaled up to multihundred-gram quantities and was developed at the Massachusetts Institute of Technology: K. C. Hultzsch; R. R. Schrock, unpublished results.
181. a) J.-M. Brunel, G. Buono, J. Org. Chem. 1993, 58, 7313-7314;
182. b) K. M. Totland, T. J. Boyd, G. G. Lavoie, W. M. Davis, R. R. Schrock, Macromolecules 1996, 29, 6114-6125.
183. R. R. Schrock, M. Wesolek, A. H. Liu, K. C. Wallace, J. C. Dewan, Inorg. Chem. 1988, 27, 2050-2054.
184. P. M. Smith, E. J. Thomas, J. Chem. Soc. Perkin Trans. 1 1998, 3541-3556.
185. a) "Collect" data-collection software, Nonius B. V., 1998;
186. b) "Scale-pack" data-processing software: Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307, (Macromolecular Crystallography, Part A);
187. c) G. M. Sheldrick, SHELX-97, Program for the refinement of crystal structures, University of Göttingen, 1997;
188. d) D. T. Cromer, J. T. Waber in International Tables for X-ray Crystallography; (Eds.: J. A. Ibers, W. C. Hamilton), Kynoch, England, 1974;
189. e) L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
190. a) J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543-2549;
191. b) T. R. Hoye, M. K. Renner, J. Org. Chem. 1996, 61, 2056-2064.