Metal-catalyzed one-step synthesis: Towards direct alternatives to multistep heterocycle and amino acid derivative formation

Chemistry - A European Journal

Volumn 15, Issue 2, 2009, Pages 302-313

  Arndtsen, Bruce A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Carbonylation; Green chemistry; Hetero cycles; Metal catalysis; Multicomponent reactions

Indexed keywords

AMIDES; AMINATION; AMINES; AMINO ACIDS; CARBONYLATION; CATALYSIS; METAL COMPLEXES; METALLIC COMPOUNDS; METALS; ORGANIC ACIDS; TRANSITION METALS;

ACID DERIVATIVE; BUILDING BLOCKS; FUNCTIONALIZED; GREEN CHEMISTRY; HETERO-CYCLES; HIGH YIELD; METAL CATALYSIS; MULTICOMPONENT REACTIONS; PRODUCT DIVERSITY;

SYNTHESIS (CHEMICAL);

AMIDE; AMINO ACID; HETEROCYCLIC COMPOUND; METAL; PEPTIDE;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

AMIDES; AMINO ACIDS; CATALYSIS; HETEROCYCLIC COMPOUNDS; METALS; PEPTIDES;

EID: 58449124067     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800767     Document Type: Article

References (149)

1. a) B. M. Trost, Science 1991, 254, 1471;
2. b) B. M. Trost, Act: Chem. Res. 2002, 35, 695.
3. a) P. A. Wender, B. L. Miller in Organic Synthesis: Theory and Applications (Ed.: T. Hudlicky), JAI, Greenwich, CT, 1993; 27;
4. b) P. A. Wender, S. T. Handy, D. L. Wright, Chem. Ind. 1997, 765.
5. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056;
6. Angew. Chem. Int. Ed. 2001, 40, 2004.
7. a) P. T. Anastas, J. C. Warner, Green Chemistry Theory and Practice, Oxford University Press, New York, 1998;
8. b) N. Winterton, Green Chem. 2001, 3, G73;
9. c) C. J. Li, T. H. Chan, Comprehensive Organic Reactions in Aqueous Media, 2nd ed., Wiley, New York, 2007;
10. d) A recent issue of Chemical Reviews was devoted to green chemistry: Chem. Rev. 2007, 107, 2167-2820.
11. a) J. C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001;
12. b) J. M. Lee, Y. Na, H. Han, S. Chang, Chem. Soc. Rev. 2004, 33, 302;
13. c) S.E. Denmark, A. Thorarensen, Chem. Rev. 1996, 96, 137;
14. d) I. Ryu, N. Sonoda, D. P. Curran, Chem. Rev. 1996, 96, 177.
15. For example: a) L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis, Wiley, New York, 2006;
16. b) A. de Meijere, S. Braise, J. Organomet. Chem. 1999, 576, 88;
17. c) M. Malarcia, Chem. Rev. 1996, 96, 289;
18. d) A. Padwa, M. D. Weingarten, Chem. Rev. 1996, 96, 223;
19. e) P. A. Wender, V. A. Verma, T. J. Paxton, T. H. Pillow, Acc. Chem. Res. 2008, 41, 40;
20. f) S. I. Ikeda, Acc. Chem. Res. 2000, 33, 611.
21. A. Strecker, Justus Liebigs Ann. Chem. 1850, 75, 27.
22. a) M. Passerini, Gazz. Chim. Ital. 1922, 52, 126;
23. b) I. Ugi, R. Meyr, Angew. Chem. 1958, 70, 702.
24. A. Hantzsch, Justus Liebigs Ann. Chem. 1882, 215, 1.
25. For representative reviews: a) J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005;
26. b) R. V. A. Orru, M. de Greef, Synthesis 2003, 10, 1471;
27. c) G. H. Posner, Chem. Rev. 1986, 86, 831;
28. d) A. Dömling, Chem. Rev. 2006, 106, 17;
29. e) C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 4957;
30. f) V. Nair, C. Rajesh, A. U. Vinod, S. Bindu, A. R. Sreekanth, J. S. Mathen, L. Balagopal, Acc. Chem. Res. 2003, 36, 899.
31. R. H. Crabtree, The Organometallic Chemistry of Transition Metals, 4th ed., Wiley-Interscience, New York, 2005.
32. a) S. E. Gibson, A. Stevenazzi, Angew. Chem. 2003, 115, 1844;
33. Angew. Chem. Int. Ed. 2003, 42, 1800;
34. b) K. M. Brummond, J. L. Kent, Tetrahedron 2000, 56, 3263.
35. a) Y. Yamamoto, S. Saito, Chem. Rev. 2000, 100, 2901;
36. b) V. Gandon, C. Aubert, M. Malacria, Chem. Commun. 2006, 2209.
37. a) A. J. von Wangelin, H. Neumann, D. Gordes, S. Klaus, D. Stüding, M. Beller, Chem. Eur. J. 2003, 9, 4286;
38. b) M. Beller, M. Eckert, Angew. Chem. 2000, 112, 1026;
39. Angew. Chem. Int. Ed. 2000, 39, 1010.
40. For representative recent examples: a) L. Ackermann, Org. Lett. 2005, 7, 439;
41. b) T. O. Vieira, H. Alper, Org. Lett. 2008, 10, 485;
42. c) G. Balme, D. Bouyssi, N. Montiere, Pure. App. Chem. 2006, 78, 231;
43. d) M. Beller, M. Eckert, W. Moradi, H. Neumann, Angew. Chem. 1999, 111, 1562;
44. Angew. Chem. Int. Ed. 1999, 38, 1454;
45. e) P. Aschwanden, C. R. J. Stephenson, E. M. Carreira, Org. Lett. 2006, 8, 2437;
46. f) I. Bae, H. Han, S. Chang, J. Am. Chem. Soc. 2005, 127, 2038;
47. g) A. Cote, A.B. Charette, J. Org. Chem. 2005, 70, 10864;
48. h) H. W. Xu, G. Y. Li, M. K. Wong, C. M. Che, Org. Lett. 2005, 7, 5349;
49. i) T. L. Church, C. M. Byrne, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2007, 129, 8156;
50. j) H. Nuske, S. Bräse, S. I. Kozhushhov, M. Noltemeyer, M. Es-Sayed, A. de Meijere, Chem. Eur. J. 2002, 8, 2350;
51. k) Y. Wang, Y. Zhu, Z. Chen, A. Mi, W. Hu, M. P. Doyle, Org. Lett. 2003, 5, 3923;
52. l) D.J. Kerr, A.C. Willis, B.L. Flynn, Org. Lett. 2004, 6, 457;
53. m) M. Whiting, V. V. Fokin, Angew. Chem. 2006, 118, 3229;
54. Angew. Chem. Int. Ed. 2006, 45, 3157;
55. n) J. L. Henderson, A. S. Edwards, M. F. Greaney, Org. Lett. 2007, 9, 5589;
56. o) H. A. Dondas, C. W. G. Fishwick, X. Gai, R. Grigg, C. Kilner, N. Dumrongchai, B. Kongkathip, N. Kongkathip, C. Polysuk, V. Sridharan, Angew. Chem. 2005,117, 7742;
57. Angew. Chem. Int. Ed. 2005, 44, 7570;
58. p) A. Arefalk, M. Marhed, A. Hallberg, J. Org. Chem. 2005, 70, 938;
59. q) R. Shintani, T. Yamagami, T. Hayashi, Org. Lett. 2006, 8, 4799;
60. r) S. I. Ikeda, D. M. Cui, Y. Sato, J. Am. Chem. Soc. 1999, 121, 4712;
61. s) K. Tonogaki, K. Itami, J. I. Yoshida, Org. Lett. 2006, 8, 1419;
62. t) S. S. Ng, T. F. Jamison, J. Am. Chem. Soc. 2005, 127, 14194;
63. u) N. Gommermann, P. Knöchel, Chem. Eur. J. 2006, 12, 4380;
64. v) Z. Liu, R. C. Larock, Angew. Chem. 2007, 119, 2587;
65. Angew. Chem. Int. Ed. 2007, 46, 2535;
66. w) K. Nitsudo, P. Thansandote, T. Wilhelm, B. Mariampillai, M. Lautens, Org. Lett. 2006, 8, 3939;
67. x) C. Wei, Z. Li, C. J. Li, Synlett 2004, 9, 1472;
68. y) M. M. McCormick, H. A. Duong, G. Zuo, J. Louie, J. Am. Chem. Soc. 2005, 127, 5030;
69. z) B. Yan, Y. Liu, Org. Lett. 2007, 9, 4323.
70. a) B. Z. Lu, W. Zhao, H. X. Wei, M, Dufour, V. Farian, C. H. Senanayake, Org. Lett. 2006, 8, 3271;
71. b) H. Quo, R. Qian, Y. Liao, S. Ma, Y. Guo, J. Am. Chem. Soc. 2005, 127, 13060;
72. c) C. D. Hopkins, H. C. Malinakova, Org. Lett. 2006, 8, 597;
73. d) D. J. Knapton, T. Y. Meyer, J. Org. Chem. 2005, 70, 785;
74. e) K. Shibata, T. Satoh, M. Miura, Org. Lett. 2005, 7, 1781;
75. f) J. Montgomery Acc. Chem. Res. 2000, 33, 457;
76. g) M. S. Mohamed, K. Kobayashi, A. Mori, Org. Lett. 2005, 7, 4487;
77. h) D.M. D'Souza, T. J. J. Müller, Chem. Soc. Rev. 2007, 36, 1095;
78. i) C. Cao, Y. Shi, A. L. Odom, J. Am. Chem. Soc. 2003, 125, 2880;
79. j) H. Ohno, Y. Ohta, S. Oishi, N. Fujii, Angew. Chem. 2007, 119, 2345;
80. Angew. Chem. Int. Ed. 2007, 46, 2295;
81. k) G. Abbiati, A. Arcadi, V. Canevari, L. Capezzuto, E. Rossi, J. Org. Chem. 2005, 70, 6454;
82. l) C. V. Galliford, K. A. Scheidt, J. Org. Chem. 2007, 72, 1811;
83. m) P. R. Andreana, C. C. Liu, S. L. Schreiber, Org. Lett. 2004, 6, 4231;
84. n) K. Oisaki, D. Zhao, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 7439;
85. o) L. C. Akullian, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2003, 115, 4376;
86. Angew. Chem. Int. Ed. 2003, 42, 4244;
87. p) M. Kimura, K. Kojima, Y. Tatsuyama, Y. Tamara, J. Am. Chem. Soc. 2006, 128, 6332;
88. q) B. M. Trost, A. B. Pinkerton, J. Am. Chem. Soc. 2002, 124, 7376;
89. r) Y. K. Chen, P. J. Walsh, J. Am. Chem. Soc. 2004, 126, 3702;
90. s) P. A. Wender, G. G. Garnber, R. D. Hubbard, S. M. Pham, L. Zhang, J. Am. Chem. Soc. 2005, 127, 2836;
91. t) K. Gao, J. Wu, J. Org. Chem. 2007, 72, 8611;
92. u) Y. Yamamoto, J. Ishii, H. Nishiyama, K. Itoh, J. Am. Chem. Soc. 2005, 127, 9625;
93. v) D. Ramon, M. Yus, Angew. Chem. 2005, 117, 1628;
94. Angew. Chem. Int. Ed. 2005, 44, 1602;
95. w) B. Hulin, L. S. Newton, S. Cabral, A. J. Walker, J. Bordner, Org. Lett. 2004, 6, 4343;
96. x) T. Dahl, C. W. Tornoe, B. Bang-Andersen, P. Nielsen, M. Jorgensen, Angew. Chem. 2008, 720, 1750;
97. Angew. Chem. Int. Ed. 2008, 47, 1726;
98. y) A. Pinto, L. Neuville, J. Zhu, Angew. Chem. 2007, 119, 3355;
99. Angew. Chem. Int. Ed. 2007, 46, 3291.
100. a) E. Bayer, Angew. Chem. 1991, 103, 117;
101. Angew. Chem. Int. Ed. Engl. 1991, 30, 113;
102. b) F. J. Sardina, H. Rapoport, Chem. Rev. 1996, 96, 1825.
103. R. D. Dghaym, K. J. Yaccato, B. A. Arndtsen, Organometallics 1998, 17, 4.
104. For a related transformation with phosphine-bound palladium complexes: S. Kacker, J. S. Kim, A. Sen, Angew. Chem. 1998, 110, 1335;
105. Angew. Chem. Int. Ed. 1998, 37, 1251.
106. a) E. Drent, P. H. M. Budzelaar, Chem. Rev. 1996, 96, 663;
107. b) F. C. Rix, M. Brookhart, P. S. White, J. Am. Chem. Soc. 1996, 118, 4746;
108. c) A. Sen, Acc. Chem. Res. 1993, 26, 303.
109. Similar results are observed with nickel and manganese complexes: a) J. L. Davis, B. A. Arndtsen, Organometallics 2000, 79, 4957;
110. b) D. Lafrance, J. L. Davis, R. Dhawan, B. A. Arndtsen, Organometallics 2001, 20, 1128;
111. c) neutral cobalt-carbonyl complexes have recently been reported to mediate an imine/CO alternating copolymerization: H. Sun, J. Zhang, Q. Liu, L. Yu, J. Zhao, Angew. Chem. 2007, 119, 6180;
112. Angew. Chem. Int. Ed. 2007, 46, 6068.
113. R. D. Dghaym, R. Dhawan, B. A. Arndtsen, Angew. Chem. 2001, 113, 3328;
114. Angew. Chem. Int. Ed. 2001, 40, 3228.
115. Representative examples: a) V. Sharma, S. Peddibhotla, J. J. Tepe, J. Am. Chem. Soc. 2006, 128, 9137;
116. b) I. H. Gilbert. D. C. Rees, A. K. Crockett, R. C. F. Jones, Tetrahedron 1995, 51, 6315;
117. c) M. R. Grimmett in Comprehensive Heterocyclic Chemistry, Vol. 5 (Eds. : A. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, p. 457.
118. R. Dhawan, R. D. Dghaym, B. A. Arndtsen, Chem. Ind. 2003, 89, 499.
119. a) "Oxazoles: Synthesis, Reactions, and Spectroscopy, Part A": G. W. Gribble Chem. Heterocycl. Compd. 2003, 60;
120. b) "Oxazoles":H. L. Gingrich, J. S. Baum., Chem. Heterocycl. Compd. 1986, 45.
121. For alternative metal-mediated approaches: a) C. A. Merlic, A. Baur, C. C. Aldrich, J. Am. Chem. Soc. 2000, 122, 7398;
122. b) H. Alper, M. Tanaka, J. Am. Chem. Soc. 1979, 101, 4245.
123. R. Dhawan, R. D. Dghaym, B. A. Arndtsen, J. Am. Chem. Soc. 2003, 125, 1474.
124. R. Dhawan, B. A. Arndtsen, J. Am. Chem. Soc. 2004, 126, 468.
125. R. Dhawan, Ph.D. Thesis, McGill University.
126. J. L. Davis, R. Dhawan, B. A. Arndtsen, Angew. Chem. 2004, 116, 600;
127. Angew. Chem. Int. Ed. 2004, 43, 590.
128. For an example of cascades involving iminium salts: Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc. 2005, 127, 15051.
129. Representative examples: a) R. R. Thompson, FASEB J. 2001, 75, 1671;
130. b) J.M. Muchowski, Adv. Med. Chem. 1992, 1, 109;
131. c) P. Cozzi, N. Mongelli, Curr. Pharm. Des. 1998, 4, 181;
132. d) A. Fürstner, H, Szillat, B. Gabor, R, Mynott, J. Am. Chem. Soc. 1998, 120, 8305.
133. P. D. Croce, R. Rerraccioli, C. La Rosa, Tetrahedron 1999, 55, 201.
134. A. R. Siamaki, B. A. Arndtsen, J. Am. Chem. Soc. 2006, 128, 6050.
135. P. D. Croce, R. Ferraccioli, C. La Rosa, Tetrahedron 1995, 51, 9385.
136. R. Dhawan, R. D. Dghaym, D. J. St. Cyr, B. A. Arndtsen, Org. Lett. 2006, 8, 3927.
137. For example: a) K. Khumtaveeporn, H. Alper, Acc. Chem. Res. 1995, 28, 414;
138. b) V. Mahadevan, Y. D. Y. L. Geltzer, G. W. Coates, Angew. Chem. 2002, 114, 2905;
139. Angew. Chem. Int. Ed. 2002, 41, 2781;
140. c) S. France, A, Weatherwax, A. E. Taggi, T. Lectka, Acc. Chem. Res. 2004, 37, 592;
141. d) L. S. Hegedus, J. Montgomery, Y. Narukawa, D. C. Snustad, J. Am. Chem. Soc. 1991, 113, 5784;
142. e) M. D. Lawlor, T. W. Lee, R. L. Danheiser, J. Org. Chem. 2000, 65, 4375.
143. Metal-Catalyzed Cross-Coupling Reactions, (Eds.: F. Diedrich, P. J. Stang), Wiley-VCH, Weinheim, 2004.
144. D. A. Black, B. A. Arndtsen, J. Org. Chem. 2005, 70, 5133.
145. D. A. Black, B. A. Arndtsen, Org. Lett. 2004, 6, 1107.
146. D. A. Black, B. A. Arndtsen, Org. Lett. 2006, 8, 1991.
147. D. A. Black, R. Beveridge, B. A. Arndtsen, J. Org. Chem. 2008, 73, 1906.
148. A. R. Siamaki, D. A. Black, B. A. Arndtsen, J. Org. Chem. 2008, 73, 1135.
149. D. A. Black, Ph.D. Thesis, McGill University.