Amidate ligand design effects in zirconium-catalyzed enantioselective hydroamination of aminoalkenes

Journal of Organometallic Chemistry

Volumn 696, Issue 1, 2011, Pages 50-60

  Ayinla, Rashidat O ^a   Gibson, Travis ^a   Schafer, Laurel L ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Axially chiral bisamides; Diastereoselective dimerization; Enantioselective aminoalkene hydroamination; Zirconium amidate complexes

Indexed keywords

AMIDATE; AXIALLY CHIRAL BISAMIDES; DIASTEREOSELECTIVE; ENANTIOSELECTIVE; HOMOCHIRAL DIMERS; HYDROAMINATIONS; IN-SITU; INTRAMOLECULAR HYDROAMINATION; LIGAND DESIGN; MONOMERIC PRECURSORS; PRECATALYSTS; PYRROLIDINES; SOLID-STATE MOLECULAR STRUCTURE; STERIC FACTOR; THERMAL STABILITY STUDIES; VARIABLE COORDINATION;

AMIDES; DESIGN; DIMERIZATION; DIMERS; ENANTIOSELECTIVITY; ISOMERS; LIGANDS; STEREOSELECTIVITY; ZIRCONIUM;

ZIRCONIUM COMPOUNDS;

EID: 78649823070     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2010.07.023     Document Type: Article

References (154)

1. For reviews on hydroamination reactions, see:
2. T.E. Mueller, K.C. Hultzsch, M. Yus, F. Foubelo, and M. Tada Chem. Rev. 108 2008 3795 3892
3. I. Aillaud, J. Collin, J. Hannedouche, and E. Schulz Dalton Trans. 2007 5105 5118
4. R. Severin, and S. Doye Chem. Soc. Rev. 36 2007 1407 1420
5. K.C. Hultzsch Adv. Synth. Catal. 347 2005 367 391
6. K.C. Hultzsch Org. Biomol. Chem. 3 2005 1819 1824
7. A.L. Odom Dalton Trans. 2005 225 233
8. S. Hong, and T.J. Marks Acc. Chem. Res. 37 2004 673 686
9. J. Seayad, A. Tillack, C.G. Hartung, and M. Beller Adv. Synth. Catal. 344 2002 795 813
10. For examples of non-enantioselective lanthanide-catalyzed hydroamination reactions, see:
11. S. Datta, M.T. Gamer, and P.W. Roesky Organometallics 27 2008 1207 1213
12. B.D. Stubbert, and T.J. Marks J. Am. Chem. Soc. 129 2007 4253 4271
13. S. Bambirra, H. Tsurugi, D. van Leusen, and B. Hessen Dalton Trans. 2006 1157 1161
14. T.K. Panda, A. Zulys, M.T. Gamer, and P.W. Roesky J. Organomet. Chem. 690 2005 5078 5089
15. G.A. Molander, and H. Hasegawa Heterocycles 64 2004 467 474
16. G.A. Molander, and E.D. Dowdy J. Org. Chem. 64 1999 6515 6517
17. V.M. Arredondo, S. Tian, F.E. McDonald, and T.J. Marks J. Am. Chem. Soc. 121 1999 3633 3639
18. V.M. Arredondo, F.E. McDonald, and T.J. Marks Organometallics 18 1999 1949 1960
19. V.M. Arredondo, F.E. McDonald, and T.J. Marks J. Am. Chem. Soc. 120 1998 4871 4872
20. Y. Li, and T.J. Marks Organometallics 15 1996 3770 3772
21. M.R. Gagne, C.L. Stern, and T.J. Marks J. Am. Chem. Soc. 114 1992 275 294
22. For examples of non-enantioselective early transition metal-catalyzed hydroamination reactions, see:
23. L. Ackermann, R. Sandmann, and L.T. Kaspar Org. Lett. 11 2009 2031 2034
24. J. Cho, T.K. Hollis, T.R. Helgert, and E.J. Valente Chem. Commun. 2008 5001 5003
25. L. Ackermann, and L.T. Kaspar J. Org. Chem. 72 2007 6149 6153
26. M.L. Buil, M.A. Esteruelas, A.M. Lopez, A.C. Mateo, and E. Onate Organometallics 26 2007 554 565
27. N. Vujkovic, B.D. Ward, A. Maisse-Francois, H. Wadepohl, P. Mountford, and L.H. Gade Organometallics 26 2007 5522 5534
28. M.A. Esteruelas, A.M. Lopez, A.C. Mateo, and E. Onate Organometallics 25 2006 1448 1460
29. H. Kim, P.H. Lee, and T. Livinghouse Chem. Commun. 2005 5205 5207
30. L.L. Anderson, J. Arnold, and R.G. Bergman Org. Lett. 6 2004 2519 2522
31. D.V. Gribkov, and K.C. Hultzsch Angew. Chem. Int. Ed. 43 2004 5542 5546
32. Y. Li, Y. Shi, and A.L. Odom J. Am. Chem. Soc. 126 2004 1794 1803
33. C. Lorber, R. Choukroun, and L. Vendier Organometallics 23 2004 1845 1850
34. B.D. Ward, A. Maisse-Francois, P. Mountford, and L.H. Gade Chem. Commun. 2004 704 705
35. V. Khedkar, A. Tillack, and M. Beller Org. Lett. 5 2003 4767 4770
36. C. Cao, Y. Shi, and A.L. Odom Org. Lett. 4 2002 2853 2856
37. A. Heutling, and S. Doye J. Org. Chem. 67 2002 1961 1964
38. T.-G. Ong, G.P.A. Yap, and D.S. Richeson Organometallics 21 2002 2839 2841
39. A. Tillack, I.G. Castro, C.G. Hartung, and M. Beller Angew. Chem. Int. Ed. 41 2002 2541 2543
40. J.S. Johnson, and R.G. Bergman J. Am. Chem. Soc. 123 2001 2923 2924
41. F. Pohlki, and S. Doye Angew. Chem. Int. Ed. 40 2001 2305 2308
42. B.F. Straub, and R.G. Bergman Angew. Chem. Int. Ed. 40 2001 4632 4635
43. E. Haak, I. Bytschkov, and S. Doye Angew. Chem. Int. Ed. 38 1999 3389 3391
44. P.J. Walsh, A.M. Baranger, and R.G. Bergman J. Am. Chem. Soc. 114 1992 1708 1719
45. For examples of non-enantioselective late transition metal-catalyzed hydroamination reactions, see:
46. R.L. Giles, J.D. Sullivan, A.M. Steiner, and R.E. Looper Angew. Chem. Int. Ed. 48 2009 3116 3120
47. A. Castonguay, D.M. Spasyuk, N. Madern, A.L. Beauchamp, and D. Zargarian Organometallics 28 2009 2134 2141
48. P.A. Dub, M. Rodriguez-Zubiri, J.-C. Daran, J.-J. Brunet, and R. Poli Organometallics 28 2009 4764 4777
49. T. Enomoto, A.-L. Girard, Y. Yasui, and Y. Takemoto J. Org. Chem. 74 2009 9158 9164
50. X. Zeng, M. Soleilhavoup, and G. Bertrand Org. Lett. 11 2009 3166 3169
51. K.D. Hesp, and M. Stradiotto Org. Lett. 11 2009 1449 1452
52. L. Ackermann, R. Sandmann, M. Schinkel, and M.V. Kondrashov Tetrahedron 65 2009 8930 8939
53. Z. Liu, and J.F. Hartwig J. Am. Chem. Soc. 130 2008 1570 1571
54. V. Lavallo, G.D. Frey, B. Donnadieu, M. Soleilhavoup, and G. Bertrand Angew. Chem. Int. Ed. 47 2008 5224 5228
55. B.M. Cochran, and F.E. Michael J. Am. Chem. Soc. 130 2008 2786 2792
56. C.F. Bender, W.B. Hudson, and R.A. Widenhoefer Organometallics 27 2008 2356 2358
57. Y. Fukumoto, H. Asai, M. Shimizu, and N. Chatani J. Am. Chem. Soc. 129 2007 13792 13793
58. A.M. Johns, Z. Liu, and J.F. Hartwig Angew. Chem. Int. Ed. 46 2007 7259 7261
59. N.T. Patil, H. Wu, and Y. Yamamoto J. Org. Chem. 72 2007 6577 6579
60. F.E. Michael, and B.M. Cochran J. Am. Chem. Soc. 128 2006 4246 4247
61. A.M. Johns, N. Sakai, A. Ridder, and J.F. Hartwig J. Am. Chem. Soc. 128 2006 9306 9307
62. C. Brouwer, and C. He Angew. Chem. Int. Ed. 45 2006 1744 1747
63. N. Morita, and N. Krause Eur. J. Org. Chem. 2006 4634 4641
64. N. Meyer, K. Loehnwitz, A. Zulys, P.W. Roesky, M. Dochnahl, and S. Blechert Organometallics 25 2006 3730 3734
65. C.F. Bender, and R.A. Widenhoefer J. Am. Chem. Soc. 127 2005 1070 1071
66. G.B. Bajracharya, Z. Huo, and Y. Yamamoto J. Org. Chem. 70 2005 4883 4886
67. L.D. Field, B.A. Messerle, K.Q. Vuong, and P. Turner Organometallics 24 2005 4241 4250
68. M. Utsunomiya, R. Kuwano, M. Kawatsura, and J.F. Hartwig J. Am. Chem. Soc. 125 2003 5608 5609
69. C.G. Hartung, A. Tillack, H. Trauthwein, and M. Beller J. Org. Chem. 66 2001 6339 6343
70. For examples of non-enantioselective groups 1 and 2 metal-catalyzed hydroamination reactions, see:
71. A.G.M. Barrett, C. Brinkmann, M.R. Crimmin, M.S. Hill, P. Hunt, and P.A. Procopiou J. Am. Chem. Soc. 131 2009 12906 12907
72. M. Arrowsmith, M.S. Hill, and G. Kociok-Kohn Organometallics 28 2009 1730 1738
73. C. Quinet, L. Sampoux, and I.E. Marko Eur. J. Org. Chem. 2009 1806 1811
74. W. Zhang, J.B. Werness, and W. Tang Org. Lett. 10 2008 2023 2026
75. M.R. Crimmin, I.J. Casely, and M.S. Hill J. Am. Chem. Soc. 127 2005 2042 2043
76. For examples of enantioselective lanthanides catalyzed-hydroamination reactions, see:
77. J. Hannedouche, I. Aillaud, J. Collin, E. Schulz, and A. Trifonov Chem. Commun. 2008 3552 3554
78. I. Aillaud, D. Lyubov, J. Collin, R. Guillot, J. Hannedouche, E. Schulz, and A. Trifonov Organometallics 27 2008 5929 5936
79. Q. Wang, L. Xiang, H. Song, and G. Zi Inorg. Chem. 47 2008 4319 4328
80. G. Zi, L. Xiang, and H. Song Organometallics 27 2008 1242 1246
81. X. Yu, and T.J. Marks Organometallics 26 2007 365 376
82. D. Riegert, J. Collin, J.-C. Daran, T. Fillebeen, E. Schulz, D. Lyubov, G. Fukin, and A. Trifonov Eur. J. Inorg. Chem. 2007 1159 1168
83. L. Xiang, Q. Wang, H. Song, and G. Zi Organometallics 26 2007 5323 5329
84. D.V. Gribkov, K.C. Hultzsch, and F. Hampel J. Am. Chem. Soc. 128 2006 3748 3759
85. H. Kim, Y.K. Kim, J.H. Shim, M. Kim, M. Han, T. Livinghouse, and P.H. Lee Adv. Synth. Catal. 348 2006 2609 2618
86. D. Riegert, J. Collin, A. Meddour, E. Schulz, and A. Trifonov J. Org. Chem. 71 2006 2514 2517
87. N. Meyer, A. Zulys, and P.W. Roesky Organometallics 25 2006 4179 4182
88. J.Y. Kim, and T. Livinghouse Org. Lett. 7 2005 1737 1739
89. D.V. Gribkov, and K.C. Hultzsch Chem. Commun. 2004 730 731
90. P.N. O'Shaughnessy, K.M. Gillespie, P.D. Knight, I.J. Munslow, and P. Scott Dalton Trans. 2004 2251 2256
91. D.V. Gribkov, F. Hampel, and K.C. Hultzsch Eur. J. Inorg. Chem. 2004 4091 4101
92. J. Collin, J.-C. Daran, E. Schulz, and A. Trifonov Chem. Commun. 2003 3048 3049
93. P.N. O'Shaughnessy, P.D. Knight, C. Morton, K.M. Gillespie, and P. Scott Chem. Commun. 2003 1770 1771
94. S. Hong, S. Tian, M.V. Metz, and T.J. Marks J. Am. Chem. Soc. 125 2003 14768 14783
95. D.V. Gribkov, K.C. Hultzsch, and F. Hampel Chem. Eur. J. 9 2003 4796 4810
96. P.N. O'Shaughnessy, and P. Scott Tetrahedron: Asymmetry 14 2003 1979 1983
97. M.A. Giardello, V.P. Conticello, L. Brard, M.R. Gagne, and T.J. Marks J. Am. Chem. Soc. 116 1994 10241 10254
98. M.R. Gagne, L. Brard, V.P. Conticello, M.A. Giardello, C.L. Stern, and T.J. Marks Organometallics 11 1992 2003 2005
99. For examples of enantioselective early transition metal-catalyzed hydroamination reactions, see:
100. G. Zi, F. Zhang, L. Xiang, Y. Chen, W. Fang, and H. Song Dalton Trans. 39 2010 4048 4061
101. G. Zi, X. Liu, L. Xiang, and H. Song Organometallics 28 2009 1127 1137
102. M.C. Wood, D.C. Leitch, C.S. Yeung, J.A. Kozak, and L.L. Schafer Angew. Chem. Int. Ed. 46 2007 354 358
103. 48, 2009. 6938.
104. A.L. Gott, A.J. Clarke, G.J. Clarkson, and P. Scott Organometallics 26 2007 1729 1737
105. D.A. Watson, M. Chiu, and R.G. Bergman Organometallics 25 2006 4731 4733
106. P.D. Knight, I. Munslow, P.N. O'Shaughnessy, and P. Scott Chem. Commun. 2004 894 895
107. For examples of enantioselective late transition metal-catalyzed hydroamination reactions, see:
108. X. Shen, and S.L. Buchwald Angew. Chem. Int. Ed. 49 2010 564 567
109. Z. Zhang, S.D. Lee, and R.A. Widenhoefer J. Am. Chem. Soc. 131 2009 5372 5373
110. J. Zhou, and J.F. Hartwig J. Am. Chem. Soc. 130 2008 12220 12221
111. L. Fadini, and A. Togni Tetrahedron: Asymmetry 19 2008 2555 2562
112. R.L. LaLonde, B.D. Sherry, E.J. Kang, and F.D. Toste J. Am. Chem. Soc. 129 2007 2452 2453
113. Z. Zhang, C.F. Bender, and R.A. Widenhoefer Org. Lett. 9 2007 2887 2889
114. N. Nishina, and Y. Yamamoto Angew. Chem. Int. Ed. 45 2006 3314 3317
115. N.T. Patil, L.M. Lutete, H. Wu, N.K. Pahadi, I.D. Gridnev, and Y. Yamamoto J. Org. Chem. 71 2006 4270 4279
116. A. Hu, M. Ogasawara, T. Sakamoto, A. Okada, K. Nakajima, T. Takahashi, and W. Lin Adv. Synth. Catal. 348 2006 2051 2056
117. J. Pawlas, Y. Nakao, M. Kawatsura, and J.F. Hartwig J. Am. Chem. Soc. 124 2002 3669 3679
118. O. Loeber, M. Kawatsura, and J.F. Hartwig J. Am. Chem. Soc. 123 2001 4366 4367
119. M. Kawatsura, and J.F. Hartwig J. Am. Chem. Soc. 122 2000 9546 9547
120. A. Togni, R. Dorta, C. Kollner, and G. Pioda Pure Appl. Chem. 70 1998 1477 1485
121. R. Dorta, P. Egli, F. Zuercher, and A. Togni J. Am. Chem. Soc. 119 1997 10857 10858
122. For examples of enantioselective groups 1 and 2 metal-catalyzed hydroamination reactions, see:
123. P. Horrillo-Martinez, and K.C. Hultzsch Tetrahedron Lett. 50 2009 2054 2056
124. T. Ogata, A. Ujihara, S. Tsuchida, T. Shimizu, A. Kaneshige, and K. Tomioka Tetrahedron Lett. 48 2007 6648 6650
125. P. Horrillo-Martinez, C. Hultzsch Kai, and F. Hampel Chem. Commun. 2006 2221 2223
126. J.A. Bexrud, and L.L. Schafer Dalton Trans. 39 2010 361 362
127. J.A. Bexrud, P. Eisenberger, D.C. Leitch, P.R. Payne, and L.L. Schafer J. Am. Chem. Soc. 131 2009 2116 2118
128. D.C. Leitch, P.R. Payne, C.R. Dunbar, and L.L. Schafer J. Am. Chem. Soc. 131 2009 18246 18247
129. L.J.E. Stanlake, and L.L. Schafer Organometallics 28 2009 3990 3998
130. D.C. Leitch, J.D. Beard, R.K. Thomson, V.A. Wright, B.O. Patrick, and L.L. Schafer Eur. J. Inorg. Chem. 2009 2691 2701
131. A.V. Lee, M. Sajitz, and L.L. Schafer Synthesis 2009 97 104
132. L.J.E. Stanlake, J.D. Beard, and L.L. Schafer Inorg. Chem. 47 2008 8062 8068
133. Z. Zhang, D.C. Leitch, M. Lu, B.O. Patrick, and L.L. Schafer Chem. Eur. J. 13 2007 2012 2022
134. J.A. Bexrud, C. Li, and L.L. Schafer Organometallics 26 2007 6366 6372
135. R.K. Thomson, J.A. Bexrud, and L.L. Schafer Organometallics 25 2006 4069 4071
136. A.V. Lee, and L.L. Schafer Organometallics 25 2006 5249 5254
137. A.V. Lee, and L.L. Schafer Synlett 2006 2973 2976
138. R.O. Ayinla, and L.L. Schafer Inorg. Chim. Acta 359 2006 3097 3102
139. R.K. Thomson, F.E. Zahariev, Z. Zhang, B.O. Patrick, Y.A. Wang, and L.L. Schafer Inorg. Chem. 44 2005 8680 8689
140. J.A. Bexrud, J.D. Beard, D.C. Leitch, and L.L. Schafer Org. Lett. 7 2005 1959 1962
141. F. Lauterwasser, P.G. Hayes, S. Braese, W.E. Piers, and L.L. Schafer Organometallics 23 2004 2234 2237
142. Z. Zhang, and L.L. Schafer Org. Lett. 5 2003 4733 4736
143. C. Li, R.K. Thomson, B. Gillon, B.O. Patrick, and L.L. Schafer Chem. Commun. 2003 2462 2463
144. A.L. Reznichenko, and K.C. Hultzsch Organometallics 29 2010 24 29
145. S.E. Denmark, and H. Matsuhashi J. Org. Chem. 67 2002 3479 3486
146. Y. Tamaru, M. Hojo, H. Higashimura, and Z. Yoshida J. Am. Chem. Soc. 110 1988 3994 4002
147. T. Kondo, T. Okada, and T.-A. Mitsudo J. Am. Chem. Soc. 124 2002 186
148. P. Eisenberger, R.O. Ayinla, J.M.P. Lauzon, and L.L. Schafer Angew. Chem. Int. Ed. 48 2009 8361 8365
149. M. Hatsuda, H. Hiramatsu, S.-I. Yamada, T. Shimizu, and M. Seki J. Org. Chem. 66 2001 4437 4439
150. For the preparation of the dichloride under reflux conditions, see:
151. S. Kano, H. Muramoto, N. Kobayashi, M. Motoi, and H. Suda Bull. Chem. Soc. Jpn. 60 1987 3659 3662
152. R.K. Thomson, Amidate complexes of the group 4 metals: synthesis, reactivity and hydroamination catalysis. Ph.D. Dissertation, University of British Columbia, Vancouver, B.C., Canada, 2008.
153. H. Song, L.-N. Gu, and G. Zi J. Organomet. Chem. 694 2009 1493 1502
154. G.R. Giesbrecht, A. Shafir, and J. Arnold Inorg. Chem. 40 2001 6069 6072