Asymmetric ion-pairing catalysis

Angewandte Chemie - International Edition

Volumn 52, Issue 2, 2013, Pages 534-561

  Brak, Katrien ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

anion binding catalysis; asymmetric catalysis; chiral anions; ion pairs; phase transfer catalysis

Indexed keywords

ANION-BINDING; ASYMMETRIC CATALYSIS; CHIRAL ANIONS; ION PAIRS; PHASE TRANSFER CATALYSIS;

NEGATIVE IONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CATALYSIS;

ION; ORGANIC COMPOUND;

CATALYSIS; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; ORGANIC CHEMISTRY; REVIEW; STEREOISOMERISM;

CATALYSIS; CHEMISTRY, ORGANIC; IONS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; ORGANIC CHEMISTRY PHENOMENA; STEREOISOMERISM;

EID: 84871966452     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201205449     Document Type: Review

References (236)

1. N. Bjerrum, K. Dan. Videsk. Selesk. Math.-Fys. Medd. 1926, 7, 3
2. M. Szwarc, Acc. Chem. Res. 1969, 2, 87-96.
3. E. V. Anslyn, D. A. Dougherty, Modern Physical Organic Chemistry, University Science Books, Sausalito, 2006.
4. S. Winstein, E. Clippinger, A. H. Fainberg, G. C. Robinson, J. Am. Chem. Soc. 1954, 76, 2597-2598
5. H. Sadek, R. M. Fuoss, J. Am. Chem. Soc. 1954, 76, 5897-5901.
6. M. S. Taylor, E. N. Jacobsen, Angew. Chem. 2006, 118, 1550-1573
7. Angew. Chem. Int. Ed. 2006, 45, 1520-1543
8. A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713-5743
9. M. Terada, Synthesis 2010, 1929-1982
10. T. Akiyama, Chem. Rev. 2007, 107, 5744-5758.
11. M. J. O'Donnell, Acc. Chem. Res. 2004, 37, 506-517
12. B. Lygo, B. I. Andrews, Acc. Chem. Res. 2004, 37, 518-525
13. T. Hashimoto, K. Maruoka, Chem. Rev. 2007, 107, 5656-5682
14. T. Ooi, K. Maruoka, Angew. Chem. 2007, 119, 4300-4345
15. Angew. Chem. Int. Ed. 2007, 46, 4222-4266
16. S.-s. Jew, H.-g. Park, Chem. Commun. 2009, 7090-7103
17. K. Maruoka, Asymmetric Phase Transfer Catalysis, Wiley-VCH, New York, 2008
18. I. Ojima, Catalytic Asymmetric Synthesis, 3 rd ed., Wiley-VCH, New York, 2010
19. T. Ooi, K. Maruoka, Acc. Chem. Res. 2004, 37, 526-533
20. U.-H. Dolling, P. Davis, E. J. J. Grabowski, J. Am. Chem. Soc. 1984, 106, 446-447.
21. J. Lacour, D. Moraleda, Chem. Commun. 2009, 7073-7089
22. G. Adair, S. Mukherjee, B. List, Aldrichimica Acta 2008, 41, 31-39.
23. Z. Zhang, P. R. Schreiner, Chem. Soc. Rev. 2009, 38, 1187-1198.
24. For a recent review on chiral anions in asymmetric catalysis, see:, R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem. 2012, 4, 603-614.
25. M. J. O'Donnell, W. D. Bennett, S. Wu, J. Am. Chem. Soc. 1989, 111, 2353-2355.
26. M. Rabinovitz, Y. Cohen, M. Halpern, Angew. Chem. 1986, 98, 958-968
27. Angew. Chem. Int. Ed. Engl. 1986, 25, 960-970.
28. D. L. Hughes, U.-H. Dolling, K. M. Ryan, E. F. Schoenwaldt, E. J. J. Grabowski, J. Org. Chem. 1987, 52, 4745-4752.
29. S. E. Denmark, R. C. Weintraub, Heterocycles 2010, 82, 1527-1540.
30. E. J. Corey, F. Xu, M. C. Noe, J. Am. Chem. Soc. 1997, 119, 12414-12415.
31. B. Lygo, P. G. Wainwright, Tetrahedron Lett. 1997, 38, 8595-8598.
32. C. Hofstetter, P. S. Wilkinson, T. C. Pochapsky, J. Org. Chem. 1999, 64, 8794-8800.
33. M. T. Reetz, Angew. Chem. 1988, 100, 1026-1030
34. Angew. Chem. Int. Ed. Engl. 1988, 27, 994-998.
35. M. T. Reetz, S. Hutte, R. Goddard, J. Am. Chem. Soc. 1993, 115, 9339-9340
36. M. T. Reetz, S. Hutte, R. Goddard, C. Robyr, Chem. Eur. J. 1996, 2, 382-384.
37. C. E. Cannizzaro, K. N. Houk, J. Am. Chem. Soc. 2002, 124, 7163-7169.
38. K. B. Lipkowitz, M. W. Cavanaugh, B. Baker, M. J. O'Donnell, J. Org. Chem. 1991, 56, 5181-5192.
39. S.-s. Jew, M.-S. Yoo, B.-S. Jeong, Y. I. Park, H.-g. Park, Org. Lett. 2002, 4, 4245-4248.
40. M.-S. Yoo, B.-S. Jeong, J.-H. Lee, H.-g. Park, S.-s. Jew, Org. Lett. 2005, 7, 1129-1131.
41. V. R. Thalladi, H. Weiss, D. Blaeser, R. Boese, A. Nangia, G. R. Desiraju, J. Am. Chem. Soc. 1998, 120, 8702-8710.
42. K. Maruoka, T. Ooi, T. Kano, Chem. Commun. 2007, 1487-1495.
43. T. Ohshima, T. Shibuguchi, Y. Fukuta, M. Shibasaki, Tetrahedron 2004, 60, 7743-7754
44. A. Okada, T. Shibuguchi, T. Ohshima, H. Masu, K. Yamaguchi, M. Shibasaki, Angew. Chem. 2005, 117, 4640-4643
45. Angew. Chem. Int. Ed. 2005, 44, 4564-4567.
46. Other binaphthyl-based chiral quaternary ammonium catalysts have also been developed, see a) T. Ooi, Y. Uematsu, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 1621-1624
47. Angew. Chem. Int. Ed. 2002, 41, 1551-1554
48. M. Kitamura, S. Shirakawa, K. Maruoka, Angew. Chem. 2005, 117, 1573-1575
49. Angew. Chem. Int. Ed. 2005, 44, 1549-1551.
50. T. Shibuguchi, Y. Fukuta, Y. Akachi, A. Sekine, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2002, 43, 9539-9543
51. T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519-6520.
52. T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 5139-5151.
53. J. Halpern, Science 1982, 217, 401-407.
54. R. He, X. Wang, T. Hashimoto, K. Maruoka, Angew. Chem. 2008, 120, 9608-9610
55. Angew. Chem. Int. Ed. 2008, 47, 9466-9468.
56. R. He, C. Ding, K. Maruoka, Angew. Chem. 2009, 121, 4629-4631
57. Angew. Chem. Int. Ed. 2009, 48, 4559-4561.
58. D. Uraguchi, Y. Asai, T. Ooi, Angew. Chem. 2009, 121, 747-751
59. Angew. Chem. Int. Ed. 2009, 48, 733-737.
60. D. Uraguchi, T. Ito, T. Ooi, J. Am. Chem. Soc. 2009, 131, 3836-3837
61. D. Uraguchi, S. Sakaki, T. Ooi, J. Am. Chem. Soc. 2007, 129, 12392-12393
62. D. Uraguchi, Y. Ueki, T. Ooi, J. Am. Chem. Soc. 2008, 130, 14088-14089
63. D. Uraguchi, Y. Ueki, T. Ooi, Science 2009, 326, 120-123.
64. For examples of other cationic phase-transfer catalysts that interact with anions primarily via H-bonding, see a) T. Kita, A. Georgieva, Y. Hashimoto, T. Nakata, K. Nagasawa, Angew. Chem. 2002, 114, 2956-2958
65. Angew. Chem. Int. Ed. 2002, 41, 2832-2834
66. K. Ohmatsu, M. Kiyokawa, T. Ooi, J. Am. Chem. Soc. 2011, 133, 1307-1309.
67. D. J. Cram, G. D. Y. Sogah, J. Chem. Soc. Chem. Commun. 1981, 625-628.
68. T. Akiyama, M. Hara, K. Fuchibe, S. Sakamoto, K. Yamaguchi, Chem. Commun. 2003, 1734-1735.
69. H. Yan, H. B. Jang, J.-W. Lee, H. K. Kim, S. W. Lee, J. W. Yang, C. E. Song, Angew. Chem. 2010, 122, 9099-9101
70. Angew. Chem. Int. Ed. 2010, 49, 8915-8917.
71. W. J. Lee, H. Yan, H. B. Jang, H. K. Kim, S.-W. Park, S. Lee, D. Y. Chi, C. E. Song, Angew. Chem. 2009, 121, 7819-7822
72. Angew. Chem. Int. Ed. 2009, 48, 7683-7686.
73. M. Fleischmann, D. Drettwan, E. Sugiono, M. Rueping, R. M. Gschwind, Angew. Chem. 2011, 123, 6488-6493
74. Angew. Chem. Int. Ed. 2011, 50, 6364-6369.
75. D. B. Llewellyn, D. Adamson, B. A. Arndtsen, Org. Lett. 2000, 2, 4165-4168.
76. D. B. Llewellyn, B. A. Arndtsen, Tetrahedron: Asymmetry 2005, 16, 1789-1799.
77. C. Carter, S. Fletcher, A. Nelson, Tetrahedron: Asymmetry 2003, 14, 1995-2004.
78. G. L. Hamilton, T. Kanai, F. D. Toste, J. Am. Chem. Soc. 2008, 130, 14984-14986.
79. T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594
80. Angew. Chem. Int. Ed. 2004, 43, 1566-1568.
81. D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357.
82. S. Mayer, B. List, Angew. Chem. 2006, 118, 4299-4301
83. Angew. Chem. Int. Ed. 2006, 45, 4193-4195.
84. J. W. Yang, M. T. H. Fonseca, N. Vignola, B. List, Angew. Chem. 2005, 117, 110-112
85. Angew. Chem. Int. Ed. 2005, 44, 108-110
86. S. G. Ouellet, J. B. Tuttle, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 32-33.
87. M. Stadler, B. List, Synlett 2008, 597-599.
88. L. Simõn, J. M. Goodman, J. Am. Chem. Soc. 2008, 130, 8741-8747.
89. X. Wang, B. List, Angew. Chem. 2008, 120, 1135-1138
90. Angew. Chem. Int. Ed. 2008, 47, 1119-1122.
91. M. Marigo, J. Franzen, T. B. Poulsen, W. Zhuang, K. A. Jorgensen, J. Am. Chem. Soc. 2005, 127, 6964-6965
92. C. Sparr, W. B. Schweizer, H. M. Senn, R. Gilmour, Angew. Chem. 2009, 121, 3111-3114
93. Angew. Chem. Int. Ed. 2009, 48, 3065-3068.
94. N. J. A. Martin, B. List, J. Am. Chem. Soc. 2006, 128, 13368-13369
95. J. Zhou, B. List, J. Am. Chem. Soc. 2007, 129, 7498-7499
96. X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070-6071.
97. O. Lifchits, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2010, 132, 10227-10229.
98. B. E. Maryanoff, H.-C. Zhang, J. H. Cohen, I. J. Turchi, C. A. Maryanoff, Chem. Rev. 2004, 104, 1431-1628.
99. M. E. Muratore, C. A. Holloway, A. W. Pilling, R. I. Storer, G. Trevitt, D. J. Dixon, J. Am. Chem. Soc. 2009, 131, 10796-10797.
100. C. A. Holloway, M. E. Muratore, R. I. Storer, D. J. Dixon, Org. Lett. 2010, 12, 4720-4723.
101. Y. Xie, Y. Zhao, B. Qian, L. Yang, C. Xia, H. Huang, Angew. Chem. 2011, 123, 5800-5804
102. Angew. Chem. Int. Ed. 2011, 50, 5682-5686.
103. M. J. Wanner, R. N. S. van der Haas, K. R. de Cuba, J. H. van Maarseveen, H. Hiemstra, Angew. Chem. 2007, 119, 7629-7631
104. Angew. Chem. Int. Ed. 2007, 46, 7485-7487.
105. N. V. Sewgobind, M. J. Wanner, S. Ingemann, R. de Gelder, J. H. van Maarseveen, H. Hiemstra, J. Org. Chem. 2008, 73, 6405-6408.
106. M. J. Wanner, R. N. A. Boots, B. Eradus, R. de Gelder, J. H. van Maarseveen, H. Hiemstra, Org. Lett. 2009, 11, 2579-2581.
107. Indolyl N-tosyl amines have also been used as carbocation precursors:, F.-L. Sun, X.-J. Zheng, Q. Gu, Q.-L. He, S.-L. You, Eur. J. Org. Chem. 2010, 47-50.
108. F.-L. Sun, M. Zeng, Q. Gu, S.-L. You, Chem. Eur. J. 2009, 15, 8709-8712.
109. Q.-X. Guo, Y.-G. Peng, J.-W. Zhang, L. Song, Z. Feng, L.-Z. Gong, Org. Lett. 2009, 11, 4620-4623.
110. T. Liang, Z. Zhang, J. C. Antilla, Angew. Chem. 2010, 122, 9928-9930
111. Angew. Chem. Int. Ed. 2010, 49, 9734-9736.
112. G. Bergonzini, S. Vera, P. Melchiorre, Angew. Chem. 2010, 122, 9879-9882
113. Angew. Chem. Int. Ed. 2010, 49, 9685-9688.
114. I. Čoric̈, S. Vellalath, B. List, J. Am. Chem. Soc. 2010, 132, 8536-8637.
115. I. Čoric̈, S. Muller, B. List, J. Am. Chem. Soc. 2010, 132, 17370-17373.
116. M. Terada, H. Tanaka, K. Sorimachi, J. Am. Chem. Soc. 2009, 131, 3430-3431.
117. Q.-W. Zhang, C.-A. Fan, H.-J. Zhang, Y.-Q. Tu, Y.-M. Zhao, P. Gu, Z.-M. Chen, Angew. Chem. 2009, 121, 8724-8726
118. Angew. Chem. Int. Ed. 2009, 48, 8572-8574.
119. Y. Takeuchi, E. Suzuki, N. Shibata, J. Am. Chem. Soc. 2000, 122, 10728-10729
120. D. Cahard, C. Audouard, J.-C. Plaquevent, N. Roques, Org. Lett. 2000, 2, 3699-3701
121. T. Ishimaru, N. Shibata, T. Horikawa, N. Yasuda, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. 2008, 120, 4225-4229
122. Angew. Chem. Int. Ed. 2008, 47, 4157-4161
123. O. Lozano, G. Blessley, T. M. del Campo, A. L. Thompson, G. T. Giuffredi, M. Bettati, M. Walker, R. Borman, V. Gouverneur, Angew. Chem. 2011, 123, 8255-8259
124. Angew. Chem. Int. Ed. 2011, 50, 8105-8109.
125. V. Rauniyar, A. D. Lackner, G. L. Hamilton, F. D. Toste, Science 2011, 334, 1681-1684.
126. R. J. Phipps, K. Hiramatsu, F. D. Toste, J. Am. Chem. Soc. 2012, 134, 8376-8379
127. A phosphoric acid-catalyzed bromination of enecarbamates that may proceed via asymmetric ion-pairing catalysis was also reported:, A. Alix, C. Lalli, P. Retailleau, G. Masson, J. Am. Chem. Soc. 2012, 134, 10389-10392.
128. U. Hennecke, C. H. Muller, R. Frolich, Org. Lett. 2011, 13, 860-863.
129. Additional reports of chiral phosphoric acid-catalyzed bromocycloetherifications that may proceed via ion-pairing catalysis: a) D. Huang, H. Wang, F. Xue, H. Guan, L. Li, X. Peng, Y. Shi, Org. Lett. 2011, 13, 6350-6353
130. S. E. Denmark, M. T. Burk, Org. Lett. 2012, 14, 256-259.
131. G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496-499.
132. R. L. LaLonde, Z. J. Wang, M. Mba, A. D. Lackner, F. D. Toste, Angew. Chem. 2010, 122, 608-611
133. Angew. Chem. Int. Ed. 2010, 49, 598-601.
134. For a review on the effects of achiral counterions on chiral ionic transition-metal complexes, see:, A. Macchioni, Chem. Rev. 2005, 105, 2039-2073.
135. Examples of transition-metal catalysis with chiral phosphates a) H. Alper, N. Hamel, J. Am. Chem. Soc. 1990, 112, 2803-2804
136. S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336-11337
137. B. Zhao, H. Du, Y. Shi, J. Org. Chem. 2009, 74, 8392-8395
138. R. Yazaki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 10275-10277
139. S. Liao, B. List, Angew. Chem. 2010, 122, 638-641
140. Angew. Chem. Int. Ed. 2010, 49, 628-631
141. V. Rauniyar, Z. J. Wang, H. E. Burks, F. D. Toste, J. Am. Chem. Soc. 2011, 133, 8486-8489
142. G. Jiang, R. Halder, Y. Fang, B. List, Angew. Chem. 2011, 123, 9926-9929
143. Angew. Chem. Int. Ed. 2011, 50, 9752-9755
144. G. Jiang, B. List, Angew. Chem. 2011, 123, 9643-9646
145. Angew. Chem. Int. Ed. 2011, 50, 9471-9474
146. G. Jiang, B. List, Chem. Commun. 2011, 47, 10022-10024
147. J. R. Zbieg, E. Yamaguchi, E. L. McInturff, M. J. Krische, Science 2012, 336, 324-327.
148. Examples of cooperative transition metal and Bronsted-acid catalysis a) V. Komanduri, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 16448-16449
149. M. Rueping, A. P. Antonchick, C. Brinkmann, Angew. Chem. 2007, 119, 7027-7030
150. Angew. Chem. Int. Ed. 2007, 46, 6903-6906
151. W. Hu, X. Xu, J. Zhou, W.-J. Liu, H. Huang, J. Hu, L. Yang, L.-Z. Gong, J. Am. Chem. Soc. 2008, 130, 7782-7783
152. C. Li, C. Wang, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 2008, 130, 14450-14451
153. C. Li, B. Villa-Marcos, J. Xiao, J. Am. Chem. Soc. 2009, 131, 6967-6969.
154. Z. Yu, W. Jin, Q. Jiang, Angew. Chem. Int. Ed. 2012, 51, 6060-6072.
155. M. Rueping, R. M. Koenigs, I. Atodiresei, Chem. Eur. J. 2010, 16, 9350-9365.
156. J. Meeuwissen, J. N. H. Reek, Nat. Chem. 2010, 2, 615-621.
157. K. Ohmatsu, M. Ito, T. Kunieda, T. Ooi, Nat. Chem. 2012, 4, 473-477.
158. D. Nakashima, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 9626-9627.
159. M. Rueping, B. J. Nachtsheim, W. Ieawsuwan, I. Atodiresei, Angew. Chem. 2011, 123, 6838-6853
160. Angew. Chem. Int. Ed. 2011, 50, 6706-6720.
161. P. Christ, A. G. Lindsay, S. S. Vormittag, J.-M. Neudorfl, A. Berkessel, A. C. O'Donoghue, Chem. Eur. J. 2011, 17, 8524-8528.
162. M. Rueping, B. J. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem. 2008, 120, 603-606
163. Angew. Chem. Int. Ed. 2008, 47, 593-596.
164. M. Rueping, B. J. Nachtsheim, Synlett 2010, 119-122.
165. M. Rueping, U. Uria, M.-Y. Lin, I. Atodiresei, J. Am. Chem. Soc. 2011, 133, 3732-3735.
166. C. H. Cheon, H. Yamamoto, J. Am. Chem. Soc. 2008, 130, 9246-9247.
167. Another example of asymmetric ion-pairing catalysis if desilylation is rate and ee-determining:, M. Sickert, C. Schneider, Angew. Chem. 2008, 120, 3687-3690
168. Angew. Chem. Int. Ed. 2008, 47, 3631-3634.
169. R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84-86.
170. M. Sickert, F. Abels, M. Lang, J. Sieler, C. Birkemeyer, C. Schneider, Chem. Eur. J. 2010, 16, 2806-2818.
171. M. Terada, Chem. Commun. 2008, 4097-4112.
172. I. D. Gridnev, M. Kouchi, K. Sorimachi, M. Terada, Tetrahedron Lett. 2007, 48, 497-500
173. L. Simõn, J. M. Goodman, J. Org. Chem. 2011, 76, 1775-1788.
174. M. Yamanaka, J. Itoh, K. Fuchibe, T. Akiyama, J. Am. Chem. Soc. 2007, 129, 6756-6764.
175. P. García-García, F. Lay, P. Garcia-Garcia, C. Rabalakos, B. List, Angew. Chem. 2009, 121, 4427-4430
176. Angew. Chem. Int. Ed. 2009, 48, 4363-4366
177. L. Ratjen, P. Garcia-Garcia, F. Lay, M. E. Beck, B. List, Angew. Chem. 2011, 123, 780-784
178. Angew. Chem. Int. Ed. 2011, 50, 754-758.
179. I. Čoric̈, B. List, Nature 2012, 483, 315-319.
180. S. Liao, E. J. Corey, W. Qinggang, B. List, J. Am. Chem. Soc. 2012, 134, 10765-10768.
181. F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646
182. G. W. Bates, M. E. Light, M. Albrecht, P. A. Gale, J. Org. Chem. 2007, 72, 8921-8927.
183. A. A. Rodriguez, H. Yoo, J. W. Ziller, K. J. Shea, Tetrahedron Lett. 2009, 50, 6830-6833
184. B. P. Hay, Chem. Soc. Rev. 2010, 39, 3700-3708.
185. M. Kotke, P. R. Schreiner, Tetrahedron 2006, 62, 434-439.
186. D. J. Tantillo, K. N. Houk, J. Comput. Chem. 2002, 23, 84-95.
187. M. Kotke, P. R. Schreiner, Synthesis 2007, 779-790.
188. M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902
189. M. S. Sigman, P. Vachal, E. N. Jacobsen, Angew. Chem. 2000, 112, 1336-1338
190. Angew. Chem. Int. Ed. 2000, 39, 1279-1281
191. P. Vachal, E. N. Jacobsen, Org. Lett. 2000, 2, 867-870.
192. S. J. Zuend, M. P. Coughlin, M. Lalonde, E. N. Jacobsen, Nature 2009, 461, 968-971.
193. S. J. Zuend, E. N. Jacobsen, J. Am. Chem. Soc. 2009, 131, 15358-15374.
194. C. S. Pan, B. List, Chem. Asian J. 2008, 3, 430-437.
195. D. A. Jose, A. Singh, A. Das, B. Ganguly, Tetrahedron Lett. 2007, 48, 3695-3698
196. S. Nishizawa, P. Buhlmann, M. Iwao, Y. Umezawa, Tetrahedron Lett. 1995, 36, 6483-6486
197. A. Allerhand, P. v. R. Schleyer, J. Am. Chem. Soc. 1963, 85, 1233-1237.
198. J. Stöckigt, A. P. Antonchick, F. Wu, H. Waldmann, Angew. Chem. 2011, 123, 8692-8719
199. Angew. Chem. Int. Ed. 2011, 50, 8538-8564.
200. M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 10558-10559.
201. D. J. Mergott, S. J. Zuend, E. N. Jacobsen, Org. Lett. 2008, 10, 745-748.
202. M. S. Taylor, N. Tokunaga, E. N. Jacobsen, Angew. Chem. 2005, 117, 6858-6862
203. Angew. Chem. Int. Ed. 2005, 44, 6700-6704.
204. I. T. Raheem, P. S. Thiara, E. A. Peterson, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 13404-13405.
205. I. T. Raheem, P. S. Thiara, E. N. Jacobsen, Org. Lett. 2008, 10, 1577-1580.
206. E. A. Peterson, E. N. Jacobsen, Angew. Chem. 2009, 121, 6446-6449
207. Angew. Chem. Int. Ed. 2009, 48, 6328-6331.
208. Y. Yamaoka, H. Miyabe, Y. Takemoto, J. Am. Chem. Soc. 2007, 129, 6686-6687.
209. R. R. Knowles, S. Lin, E. N. Jacobsen, J. Am. Chem. Soc. 2010, 132, 5030-5032.
210. R. Thoma, T. Schulz-Gasch, B. D'Arcy, J. Benz, J. Aebi, H. Dehmlow, M. Hennig, M. Stihle, A. Ruf, Nature 2004, 432, 118-122.
211. C. T. Calderone, D. H. Williams, J. Am. Chem. Soc. 2001, 123, 6262-6267.
212. S. E. Reisman, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 7198-7199.
213. A. R. Brown, W.-H. Kuo, E. N. Jacobsen, J. Am. Chem. Soc. 2010, 132, 9286-9288.
214. J. A. Birrell, J.-N. Desrosiers, E. N. Jacobsen, J. Am. Chem. Soc. 2011, 133, 13872-13875.
215. T. R. Kelly, M. H. Kim, J. Am. Chem. Soc. 1994, 116, 7072-7080.
216. A nonstereoselective application of this principle:, T. Weil, M. Kotke, C. M. Kleiner, P. R. Schreiner, Org. Lett. 2008, 10, 1513-1516.
217. R. S. Klausen, E. N. Jacobsen, Org. Lett. 2009, 11, 887-890.
218. Y. Lee, R. S. Klausen, E. N. Jacobsen, Org. Lett. 2011, 13, 5564-5567.
219. R. S. Klausen, A. M. Hyde, E. N. Jacobsen, unpublished results.
220. J. Seayad, A. M. Seayad, B. List, J. Am. Chem. Soc. 2006, 128, 1086-1087.
221. N. Z. Burns, M. R. Witten, E. N. Jacobsen, J. Am. Chem. Soc. 2011, 133, 14578-14581.
222. G. C. Fu, Acc. Chem. Res. 2004, 37, 542-547.
223. K. C. De, E. G. Klauber, D. Seidel, J. Am. Chem. Soc. 2009, 131, 17060-17061
224. E. G. Klauber, K. C. De, T. K. Shah, D. Seidel, J. Am. Chem. Soc. 2010, 132, 13624-13626
225. N. Mittal, D. X. Sun, D. Seidel, Org. Lett. 2012, 14, 3084-3087.
226. E. G. Klauber, N. Mittal, T. K. Shah, D. Seidel, Org. Lett. 2011, 13, 2464-2467.
227. K. C. De, D. Seidel, J. Am. Chem. Soc. 2011, 133, 14538-14541.
228. K. C. De, N. Mittal, D. Seidel, J. Am. Chem. Soc. 2011, 133, 16802-16805.
229. G. E. Veitch, E. N. Jacobsen, Angew. Chem. 2010, 122, 7490-7493
230. Angew. Chem. Int. Ed. 2010, 49, 7332-7335.
231. H. Xu, S. J. Zuend, M. G. Woll, Y. Tao, E. N. Jacobsen, Science 2010, 327, 986-990.
232. R. R. Knowles, E. N. Jacobsen, Proc. Natl. Acad. Sci. USA 2010, 107, 20678-20685.
233. L. Pauling, Chem. Eng. News 1946, 24, 1377
234. W. P. Jencks, Catalysis in Chemistry and Enzymology, McGraw Hill, New York, 1989.
235. M. G. Chudzinski, C. A. McClary, M. S. Taylor, J. Am. Chem. Soc. 2011, 133, 10559-10567.
236. K. N. Houk, P. H.-Y. Cheong, Nature 2008, 455, 309-313.