Asymmetric synthesis of tertiary alcohols and α-tertiary amines via Cu-catalyzed C - C bond formation to ketones and ketimines

Chemical Reviews

Volumn 108, Issue 8, 2008, Pages 2853-2873

  Shibasaki, Masakatsu ^a   Kanai, Motomu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINATION; AMINES; CATALYSIS; CHEMICAL BONDS; CHEMICAL REACTIONS; CHEMISTRY; CHLORINE COMPOUNDS; COPPER; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; KETONES; MOLECULES; SUBSTRATES; SYNTHESIS (CHEMICAL);

KETIMINES; TERTIARY ALCOHOLS; TERTIARY AMINES;

ORGANIC COMPOUNDS;

ALCOHOL DERIVATIVE; AMINE; COPPER; KETAMINE; KETONE; ORGANOMETALLIC COMPOUND;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; REVIEW; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; AMINES; CATALYSIS; COPPER; KETAMINE; KETONES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 51049122384     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr078340r     Document Type: Review

References (211)

1. The Sharpless asymmetric dihydroxylation of trisubstituted olefins can produce enantiomerically-enriched tertiary alcohols. For review, see: Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 357-398.
2. For recent examples of catalytic enantioselective α-oxidation of carbonyl groups to produce tertiary alcohols, see (a) Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S. J. Am. Chem. Soc. 2006, 128, 16488.
3. (b) Toullec, P. Y.; Bonaccorsi, C.; Mezzetti, A.; Togni, A. Proc. Natl. Acad Sci. U. S.A. 2004, 101, 5810 This reaction pattern produces α,α-disubstituted α-hydroxyl carboxylic acid derivatives.
4. For recent examples of catalytic enantioselective electrophilic α-amination of carbonyl compounds to produce α-tertiary amines, see (a) Terada, M.; Nakano, M.; Ube, H. J. Am. Chem. Soc. 2006, 128, 16044.
5. (b) Saaby, S.; Bella, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 8120.
6. (c) Mashiko, T.; Hara, K.; Tanaka, D.; Fujiwara, Y.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 11342.
7. (d) Kano, T.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2006, 128, 2174. (1,3-dipolar cycloaddition). This reaction pattern produces α,α-disubstituted α-amino acid derivatives.
8. For reviews of catalytic asymmetric synthesis of tetrasubstituted carbons, see (a) Riant, O.; Hannedouche, J. Org. Biomol. Chem. 2007, 5, 873.
9. (b) Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 5969.
10. (c) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
11. (d) Hatano, M.; Ishihara, K. Synthesis 2008, 1647.
12. For the pioneering work of catalytic enantioselective C-C bond-formation to simple ketones, see (e) Dosa, P. I.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 445.
13. In addition to the reactions described in this review, cyanation of ketones and ketimines are the most intensively studied catalytic asymmetric tetrasubstituted carbon synthesis. However, there are no copper-catalyzed reactions in this category. For examples of catalytic eantioselective cyanation of ketones, see (a) Belokon, Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Tararov, V. I. Tetrahedron Lett. 1999, 38, 6669.
14. (b) Belokon', Y. N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N. S.; Khrustalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M.; Timofeeva, G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968.
15. (c) Hamashima, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 7412.
16. (d) Hamashima, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 691.
17. (e) Yabu, K.; Masumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908.
18. (f) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195.
19. (g) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900.
20. (h) Deng, H.; Isler, M. P.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2002, 41,
21. (i) Riu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 5384.
22. (j)Fuerst, D. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 8964.
23. (k) Liu, X.; Qin, B.; Zhou, X.; He, B.; Feng, X. J. Am. Chem. Soc. 2005, 127, 12224.
24. For catalytic enantioselective Strecker reaction of ketimines and related reactions, see (a) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
25. (b) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
26. (c) Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Vallée, Y. Tetrahedron: Asymmetry 2001, 12, 1147.
27. (d) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634.
28. (e) Kato, N.; Suzuki, M.; Kariai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3147.
29. (f) Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3153.
30. (g) Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784.
31. (h) Shibasaki, M.; Kanai, M.; Mita, T. Org. React. 2008, 70, 1.
32. For examples, see (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.
33. (b) Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490.
34. For examples, see (a) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1966, 5239.
35. (b) Salomon, R. G.; Kochi, J. K. J. Am. Chem. Soc. 1973, 95, 3300.
36. Review (c) Dave, V.; Warnhoff, E. W. Org. React. 1970, 18, 217.
37. For examples, see (a) Kwart, H.; Kahn, A. A. J. Am. Chem. Soc. 1997, 89, 1950.
38. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744.
39. (c) Evans, D. A.; Fad, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
40. (d) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889.
41. (a) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893.
42. (b) Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686.
43. For other examples of Cu(II)-box (or pybox) catalyzed asymmetric reactions, see (a) Evans, D..; Miller, S. J.; Lectka, T. C. J. Am. Chem. Soc. 1993, 115, 6460. (Diels - Alder reaction).
44. (b) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Connell, B. T. J. Am. Chem. Soc. 1999, 121, 669. (aldol reaction).
45. (c) Evans, D. A.; Johnson, J. S. J. Am. Chem. Soc. 1998, 120, 4895. (hetero Diels-Alder reaction).
46. (d) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824. (carbonyl-ene reaction)
47. Movassaghi, M.; Piizzi, G.; Siegel, D. S.; Piersanti, G. Angew. Chem., Int. Ed. 2006, 45, 5859.
48. (a) van Lingen, H. L.; van de Mortel, J. K. W.; Kekking, K. F. W.; van Delft, F. L.; Songinke, T.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2003, 317.
49. (b) van Lingen, H. L.; van Delft, F. L.; Storcken, R. P. M.; Hekking, K. F. W.; Klaassen, A.; Smits, J. J. M.; Ruskowska, P.; Frelek, J.; Rutjes, F. P. J. T. Eur. J. Org., Chem. 2005, 4975.
50. Simonelli, B.; Orlandi, S.; Benaglia, M.; Pozzi, G. Eur. J. Org. Chem. 2004, 2669.
51. (a) Langer, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
52. Langer, M.; Rémy, P.; Bolm, C. Chem. - Eur. J. 2005, 11, 6254.
53. Brandt, J.; Gais, H. J. Tetrahedron: Asymmetry 1997, 8, 909.
54. 2OH in catalytic asymmetric Michael-type reaction, see Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994.
55. For a review of catalytic asymmetric vinylogous aldol reactions, see Denmark, S. E.; Heemstra, J. R., Jr.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682.
56. Rémy, P.; Langner, M.; Bolm, C. Org. Lett. 2006, 8, 1209.
57. Le, J. C.-D.; Pagenkopf, B. L. Org. Lett. 2004, 6, 4097.
58. Trost, B. M. Science 1991, 254, 1471.
59. For the first example of a catalytic asymmetric nitroaldol reaction of aldehydes, see (a) Sasai, H.; Suzuki, S.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418.
60. (b) For a review, see Shibasaki, M.; Gröger, H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin-Heidelberg, 1999; Chapter 29.3.
61. (a) Christensen, C.; Juhl, K.; Jørgensen, K. A. Chem. Commun. 2001, 2222.
62. (b) Christensen, C.; Juhl, K.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 4875.
63. (a) Lu, S.-F.; Du, D. M.; Zhang, S.-W.; Xu, J. Tetrahedron: Asymmetry 2004, 15, 3433.
64. (b) Du, D.-M.; Lu, S.-F.; Fang, T.; Xu, J. J. Org. Chem. 2005, 70, 3712.
65. Makino, K.; Ogawa, I.; Hamada, Y. Heterocycles 2005, 66, 433.
66. For the first example of a catalytic enantioselective direct aldol reaction of aldehydes, see (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1997, 36, 1871.
67. (b) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M J. Am. Chem. Soc. 1999, 121, 4168.
68. (c) For a review, see Shibasaki, M.; Yoshikawa, N.; Matsunaga, S. In Comprehensive Asymmetric Catalysis, Supplement 1; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin-Heidelberg, 2004; Chapter 29.4.
69. Gathergood, N.; Juhl, K.; Poulsen, T. B.; Thordrup, K.; Jorgensen, K. A. Org. Biol. Chem. 2004, 2, 1077.
70. (a) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837.
71. (b) Pagenkopf, B. L.; Krüger, J.; Stojanovic, A.; Carreira, E. M. Angew. Chem., Int. Ed. 1998, 37, 3124.
72. Oisaki, K.; Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5644.
73. (a) Oisaki, K.; Zhao, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7164.
74. (b) For a preliminary ligand optimization, see Oisaki, K.; Zhao, D.; Suto, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2005, 46, 4325.
75. (a) For the first example of a catalytic enantioselective aldol reaction of ketones, see Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233.
76. (b) Denmark, S. E.; Fan, Y.; Eastgate, M. D. J. Org. Chem. 2005, 70, 5235.
77. (a) Ireland, T.; Tappe, K.; Grossheimann, G.; Knochel, P. Chem. - Eur. J. 2002, 8, 843.
78. The structure of Taniaphos in this original paper was incorrect (personal communication from Prof. Knochel). (b) Fukuzawa, S-i.; Yamamoto, M.; Hosaka, M.; Kikuchi, S. Eur. J. Org. Chem. 2007, 5540.
79. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
80. CuF itself is unstable and not isolable in the absence of phosphine ligands. See (a) Cotton, F. A.; Wilkinson, G.; Murrillo; C. A.; Bochmann, M. In Advanced Inorganic Chemistry; Wiley-Interscience: New York, 1999.
81. 3-2EtOH complex is a well-characterized, stable CuF complex. See Gulliver, D. J.; Levason, W.; Webster, M. Inorg. Chim. Acta 1981, 52, 153.
82. Suto, Y.; Kumagai, N.; Matsunaga, S.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 3147.
83. Suto, Y.; Kanai, M.; Shibasaki, M. Unpublished result. In ref 36, a preliminary result using CuF-tol-BINAP as the catalyst was reported (48%, 49% ee, at -30 °C for 85 h).
84. Moreau, X.; Bazán-Tejeda, B.; Campagne, J.-M. J. Am. Chem. Soc. 2005, 127, 7288.
85. Lam, H. W.; Joensuu, P. M. Org. Lett. 2005, 7, 4225.
86. For examples of catalytic asymmetric reductive aldol reactions of aldehydes, see (a) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528.
87. (b) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
88. (c) Russell, A. E; Fuller, N. O.; Taylor, S. J.; Aurriset, P.; Morken, J. P. Org. Lett. 2004, 6, 2309.
89. (d) Nishiyama, H.; Shiomi, T.; Tsuchiya, Y.; Matsuda, I. J. Am. Chem. Soc. 2005, 127, 6972.
90. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.
91. Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Helv. Chim. Acta 1991, 74, 370.
92. For examples of Cu-catalyzed asymmetric conjugate reduction, see (a) Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473.
93. (b) Lipshutz, B. H.; Servesko J. M.; Taft, B. R. J. Am. Chem. Soc. 2004, 126, 8352. See also the chapter written by Krause and Lipshutz in this issue.
94. Deschamp, J.; Chuzel, O.; Hannedouche, J.; Riant, O. Angew. Chem., Int. Ed. 2006, 45, 1292.
95. (a) Zhao, D.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128,14440.
96. (b) Zhao, D.; Oisaki, K.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2006, 47, 1403.
97. Recent examples of catalytic asymmetric alkylative aldol reactions to aldebydes (a) Yoshida, K.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 10984.
98. (b) Nicolaou, K. C.; Tang, W.; Dagneau, P.; Faraoni, R. Angew. Chem., Int. Ed. 2005, 44, 3874.
99. (c) Brown, M. K.; Degrado, S. J.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2005, 44, 5306.
100. (d) Howell, G. P.; Fletcher, S. P.; Geurts, K.; ter Horst, B.; Feringa, B. L. J. Am. Chem. Soc. 2006, 128, 14977.
101. Oisaki, K.; Zhao, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 7439.
102. Jeulin, S.; de Paule, S. D.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Angew. Chem., Int. Ed. 2004, 43, 320.
103. For reviews of asymmetric Mannich reactions, see (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
104. (b) Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
105. (c) Marques, M. M. B. Angew. Chem., Int. Ed. 2006, 45, 348.
106. Tetrasubstituted carbon-forming catalytic enantioselective Mannich reactions of special ketoiminoesters have been reported by Jørgensen, see (a) Saaby, S.; Nakama, K.; Lie, M. A.; Hazell, R. G.; Jørgensen, K. A. Chem. -Eur. J. 2003, 9, 6145. (Zn catalysis).
107. (b) Zhuang, W.; Saaby, S.; Jørgensen, K. A. Angew. Chem. Int. Ed 2004, 43, 4476. (organocatalysis).
108. For a general diastereoselective synthesis of β,β-disubstituted amino acids, see (c) Minter, A. R.; Fuller, A. A.; Mapp, A. K. J. Am. Chem. Soc. 2003, 125, 6846.
109. (d) Fuller, A. A.; Chen, B.; Minter, A. R.; Mapp, A. K. J. Am. Chem. Soc. 2005, 127, 5376.
110. Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 500.
111. Corbett, J. W.; Ko, S. S.; Rodgers, J. D.; Gearhart, L. A.; Magnus, N. A.; Bacheler, L. T.; Diamond, S.; Jeffrey, S.; Klabe, R. M.; Cordova, B. C.; Garber, S.; Logue, K.; Trainor, G. L.; Anderson, P. S.; Erickson-Vittanen, S. K. J. Med. Chem. 2000, 43, 2019.
112. Pierce, M. E.; Parsons, R. L., Jr.; Radesca, L. A.; Lo, Y. S.; Silverman, S.; Moore, J. R.; Islam, Q.; Choudhury, A.; Fortunak, J. M. D.; Nguyen, D.; Luo, C.; Morgan, S. J.; Davis, W. P.; Confalone, P. N.; Chen, C.; Tillyer, R. D.; Frey, L.; Tan, L.; Xu, F.; Zhao, D.; Thompson, A. S.; Corley, E. G.; Grabowski, E. J. J.; Reamer, R.; Reider, P. J. J. Org. Chem. 1998, 63, 8536.
113. Cozzi, P. G. Angew. Chem., Int. Ed. 2003, 42, 2895.
114. For other examples of catalytic enantioselective addition of zinc acetylide to ketones not using a copper catalyst, see (a) Wang, Q.; Zhang, B.; Hu, G.; Chen, C.; Zhao, Q.; Wang, R. Org. Biomol. Chem. 2007, 5, 1161,
115. and references cited thereinFor a review of catalytic enantioselective alkynylation of ketones, see (b) Pu, L. Tetrahedron 2003, 59, 9873.
116. Lu, G.; Li, X.; Jia, X.; Chan, W. L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2003, 42, 5057.
117. Motoki, R.; Tomita, D.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2006, 47, 8083.
118. (a) Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
119. (b) Fässler, C. S.; Tomooka, C. S.; Frantz, D. E.; Carreira, E. M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5843.
120. For other selected examples of catalytic enantioselective alkynylation of aldehydes, see (a) Takita, R.; Yakura, K.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127,13760.
121. (b) Yamashita, M.; Yamada, K.i.; Tomioka, K. Adv. Synth. Catal. 2005, 347,1649.
122. (c) Emmerson, D. P. G.; Hems, W. P.; Davis, B. G. Org. Lett. 2006, 8, 207. Selected examples of catalytic enantioselective alkynylation of aldimines:
123. (d) Wei, C.; Li, C. J. J. Am. Chem. Soc. 2002, 124, 5638.
124. (e) Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2003, 42, 5763.
125. (f) Bisai, A.; Singh, V. K Org. Lett. 2006, 8, 2405. Catalytic enantioselective alkynylation of ketimines has yet to be developed.
126. Jiang, B.; Chen, Z.; Tang, X. Org. Lett. 2002, 4, 3451.
127. Tsuda, T.; Hashimoto, T.; Saegusa, T. J. Am. Chem. Soc. 1972, 94, 658.
128. Suto, Y.; Tsuji, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 3757.
129. Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
130. Motoki, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2007, 9, 2997.
131. Maruoka, K.; Hoshino, Y.; Shirasaka, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967.
132. For examples of catalytic enantioselective carbonyl-ene reactions of glyoxylates, see (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949.
133. (b) Yuan, Y.; Zhang, X.; Ding, K. Angew. Chem., Int. Ed. 2003, 42, 5478.
134. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936.
135. Yang, D.; Yang, M.; Zhu, N.-Y. Org. Lett. 2003, 5, 3749.
136. Langner, M.; Rémy, P.; Bolm, C. Synlett 2005, 781.
137. For representative reviews, see (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
138. (b) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763.
139. (c) Ding, H.; Friestad, G. K. Synthesis 2005, 2815.
140. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467.
141. (b) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Rochi, A. J. Am. Chem. Soc. 1993, 115, 7001.
142. For examples of catalytic enantioselective allylation of ketones using allyltin reagents, see (a) Tagliavini, E.; Casolari, S.; D'Addario, D. Org. Lett. 1999, 1, 1061.
143. (b) Cunningham, A.; Woodward, S. Synthesis 2002, 43.
144. (c) Waltz, K. M.; Gavenonis, J.; Walsh, P. J. Angew. Chem., Int. Ed. 2002, 41, 3697.
145. (d) Kii, S.; Maruoka, K. Chirality 2003, 15, 67.
146. (e) Teo, Y.-C.; Goh, J.-D.; Loh, T.-P. Org. Lett. 2005, 7, 2743.
147. (f) Wooten, A. J.; Kim, J. G.; Walsh, P. J. Org. Lett. 2007, 9, 381.
148. (g) Zhang, X.; Chen, D.; Liu, X.; Feng, X. J. Org. Chem. 2007, 72, 5227.
149. Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 6536.
150. Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910.
151. For a recent paper discussing the metallotropic equilibrium of allyllic metal compounds, see Sklute, G.; Marek, I. J. Am. Chem. Soc. 2006, 128, 4642.
152. Wadamoto, M.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 14556.
153. Yanagisawa, A.; Kageyama, H.; Nakatsuka, Y.; Asakawa, K.; Matsumoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 1999, 38, 3701.
154. Lou, S.; Moquist, P.; Schaus, S. E. J Am. Chem. Soc. 2006, 128, 12660.
155. For examples of enhancing the reactivity of allylboronate by increasing the Lewis acidity of the boron via coordination of the alkoxy ligand to catalytic Lewis acid metals, see (a) Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 11586.
156. (b) Ishiyama, T.; Ahiko, T.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 12414.
157. (c) Rauniyar, V.; Hall, D. G. J. Am. Chem. Soc. 2004, 126, 4518.
158. Miller, J. J.; Sigman, M. S. J. Am. Chem. Soc. 2007, 129, 2752.
159. Wada, R.; Shibuguchi, T.; Makino, S.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 7687.
160. For a general asymmetric allylation of ketone-derived N-acyl hydrazones using a chiral allylsilane, see Berger, R.; Duff, K.; Leighton, J. L. J. Am. Chem. Soc. 2004, 126, 5686.
161. Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192.
162. Kanai, M.; Wada, R.; Shibuguchi, T.; Shibasaki, M. Pure Appl. Chem. 2008, 80, 1055.
163. Catalytic enantioselective addition of aryl and alkenyl groups to simple ketones requires organozinc reagents as nucleophiles. For examples, see (a) Ramón, D. J.; Yus, M. Tetrahedron Lett. 1998, 39, 1239.
164. (b) Ramón, D. J.; Yus, M. Tetrahedron 1998, 54, 5651.
165. (c) Garcia, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970.
166. (d) Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 8355.
167. Review (e) Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2004, 43, 284.
168. Review (f) Betancort, J. M.; García, C.; Walsh, P. J. Synlett 2004, 749.
169. Zhuang, W.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2001, 66, 1009.
170. Corma, A.; García, H.; Moussaif, A.; Sabater, M. J.; Zniber, R.; Redouane, A. Chem. Commun. 2002, 1058.
171. Lyle, M. P. A.; Draper, N. D.; Wilson, P. D. Org. Lett. 2005, 7, 901.
172. Zhao, J.-L.; Liu, L.; Sui, Y.; Liu, Y.-L.; Wang, D.; Chen, Y.-J. Org. Lett. 2006, 8, 6127.
173. (a) Tomita, D.; Wada, R.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 4138.
174. (b) Tomita, D.; Kanai, M.; Shibasaki, M. Chem. Asian J. 2006, 1, 161.
175. For example Nishihara, Y.; Ikegashira, K.; Toriyama, F.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 985.
176. (a) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976.
177. (b) Fujihara, H.; Nagai, K.; Tomioka, K. J. Am. Chem. Soc. 2000, 122, 12055.
178. (c) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409.
179. (d) Dahmen, S.; Bräse, S. J. Am. Chem. Soc. 2002, 124, 5940.
180. (e) Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 1692.
181. (f) Boezio, A. A.; Pytkowicz, J.; Côté, A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 14260.
182. (g) See also Tomioka's chapter in this thematic issue.
183. Lauzon, C.; Charette, A. B. Org. Lett. 2006, 8, 2743.
184. (a) Ramón, D. J.; Yus, M. Tetrahedron 1998, 54, 5651.
185. (b) García, C.; LaRochelle, L. K.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10970.
186. (c) Jeon, S.-J.; Li, H.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 16416.
187. (d) Forrat, V. J.; Pieto, O.; Ramón, D. J.; Yus, M. Chem. - Eur. J. 2006, 12, 4431.
188. (e) Hatano, M.; Miyamoto, T.; Ishihara, K. Org. Lett. 2007, 9, 4535.
189. Danishefsky, S.; Kitahara, T. J. Am. Chem. Soc. 1974, 96, 7807.
190. (a) Johannsen, M.; Yao, S.; Jørgensen, K. A. Chem. Commun. 1997, 2169.
191. (b) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1998, 120, 8599. For a review of catalytic asymmetric hetero-Diels-Alder-type reaction of ketones, see.
192. (c) Jørgensen, K. A. Eur. J. Org. Chem. 2004, 2093.
193. Ghosh, A. K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231.
194. Dalko, P. I.; Moisan, L.; Cossy, J. Angew. Chem., Int. Ed. 2002, 41, 625.
195. For other examples of catalytic asymmetric hetero-Diels - Alder-type reaction of activated ketones (pyruvates), see (a) Furuno, H.; Kambara, T.; Tanaka, Y.; Hanamoto, T.; Kagawa, T.; Inanaga, J. Tetrahedron Lett. 2003, 44, 6129. (rare earth metal catalyst).
196. (b) Zhuang, W.; Poulsen, T. B.; Jørgensen, K. A. Org. Biomol. Chem. 2005, 3, 3284. (organocatalyst)
197. Landa, A.; Richter, B.; Johansen, R. L.; Minkkilä, A.; Jørgensen, K. A. J. Org. Chem. 2007, 72, 240.
198. For examples, see (a) Cabrera, S.; Gómez-Arrayás, R.; Carretero, J. C. J. Am. Chem. Soc. 2005, 127, 16394.
199. (b) Yan, X.-X.; Peng, Q.; Zhang, Y.; Zhang, K.; Hong, W.; Hou, X.-L.; Wu, Y.-D. Angew. Chem., Int. Ed. 2006, 45, 1979.
200. (c) Oderaotoshi, Y.; Cheng, W.; Fujitomi, S.; Kasano, Y.; Minakata, S.; Komatsu, M. Org. Lett. 2003, 5, 5043.
201. (d) Carrera, S.; Arrayás, R. G.; Martín-Matute, B.; Cossío, F. P.; Carretero, J. C. Tetrahedron 2007, 63, 6587.
202. (e) Llamas, T.; Arrayás, R. G.; Carretero, J. C. Synthesis 2007, 950.
203. (f) Review Nájera, C.; Sansano, J. M. Angew. Chem., Int. Ed. 2005, 44, 6272.
204. For examples of asymmetric [3 + 2] cycloadditions other than using Cu catalyst, see (a) Gothelf, A. S.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 4236. (Zn).
205. (b) Longmire, J. M.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 13400. (Ag).
206. (c) Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174. (Ag).
207. (d) Knöpfel, T. F.; Aschwanden, P.; Ichikawa, T.; Watanabe, T.; Carreira, E. M. Angew. Chem., Int. Ed. 2004, 43, 5971. (Ag)
208. Cross-coupling reactions and olefin metathesis are typical examples.
209. Three reports relevant to this chapter appeared during the review. See Sedelmeier, J.; Hammerer, T.; Bolm, C. Org. Lett. 2008, 10, 817.
210. (b) Doherty, S.; Goodrich, P.; Hardacre, C.; Pârvulescu, V.; Paun, C. Adv. Synth. Catal. 2008, 350, 295.
211. (c) Mandoli, A.; Lessi, M.; Pini, D.; Evangelisti, C.; Salvadori, P. Adv. Synth. Catal. 2008, 350, 375.