Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling

Journal of Organic Chemistry

Volumn 77, Issue 10, 2012, Pages 4503-4515

  Boyce, Gregory R ^a   Greszler, Stephen N ^a   Johnson, Jeffrey S ^a   Linghu, Xin ^a   Malinowski, Justin T ^a   Nicewicz, David A ^a   Satterfield, Andrew D ^a   Schmitt, Daniel C ^a   Steward, Kimberly M ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC REACTIONS; GLYCOLIC ACIDS; GLYOXYLATE; KETO ESTER; MULTI-COMPONENT COUPLING; MULTICOMPONENT COUPLING REACTIONS; NATURAL PRODUCTS; REACTION MODES; STRUCTURAL DIVERSITY; SYNTHETIC EQUIVALENTS; SYNTHONS;

FUNCTIONAL GROUPS;

CATALYSIS;

ESTER; FUNCTIONAL GROUP; GLYCOLIC ACID; GLYOXYLIC ACID DERIVATIVE; NATURAL PRODUCT; REAGENT;

CATALYSIS; CHEMICAL REACTION; ELECTROPHILICITY; MULTICOMPONENT COUPLING REACTION; NUCLEOPHILICITY; REVIEW; STRUCTURE ANALYSIS;

CATALYSIS; GLYOXYLATES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; STEREOISOMERISM;

EID: 84862062334     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300184h     Document Type: Review

References (144)

1. Coppola, G. M.; Schuster, H. F. Chiral α-Hydroxy Acids in Enantioselective Synthesis; Wiley-VCH: Weinheim, 1997.
2. Cristau, H.-J.; Marat, X.; Vors, J.-P.; Virieux, D.; Pirat, J.-L. Curr. Org. Synth. 2005, 2, 113-119
3. Bertrand, M. B.; Wolfe, J. P. Org. Lett. 2006, 8, 4661-4663
4. Giampietro, N. C.; Kampf, J. W.; Wolfe, J. P. J. Am. Chem. Soc. 2009, 131, 12556-12557
5. Moser, W. H. Tetrahedron 2001, 57, 2065-2084
6. Page, P. C. B.; McKenzie, M. J. Product Subclass 25: Acylsilanes. In Science of Synthesis; Fleming, I., Ed.; Thieme: Stuttgart, 2001; Vol. 4, pp 513-568.
7. Patrocinio, A. F.; Moran, P. J. S. J. Braz. Chem. Soc 2001, 12, 7-31
8. Cirillo, P. F.; Panek, J. S. Org. Prep. Proced. Int. 1992, 24, 553-582
9. Page, P. C. B.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195
10. Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84
11. Degl'Innocenti, A.; Ricci, A.; Mordini, A.; Reginato, G.; Colotta, V. Gazz. Chim. Ital. 1987, 117, 645-648
12. Reich, H. J.; Holtan, R. C.; Bolm, C. J. Am. Chem. Soc. 1990, 112, 5609-5617
13. Takeda, K.; Ohnishi, Y. Tetrahedron Lett. 2000, 41, 4169-4172
14. Linghu, X.; Nicewicz, D. A.; Johnson, J. S. Org. Lett. 2002, 4, 2957-2960
15. Linghu, X.; Johnson, J. S. Angew. Chem., Int. Ed. 2003, 42, 2534-2536
16. Nicewicz, D. A.; Yates, C. M.; Johnson, J. S. Angew. Chem., Int. Ed. 2004, 43, 2652-2655
17. Nicewicz, D. A.; Yates, C. M.; Johnson, J. S. J. Org. Chem. 2004, 69, 6548-6555
18. Bausch, C. C.; Johnson, J. S. J. Org. Chem. 2004, 69, 4283-4285
19. Linghu, X.; Bausch, C. C.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 1833-40
20. Tarr, J. C.; Johnson, J. S. J. Org. Chem. 2010, 75, 3317-3325
21. Takeda, K.; Tanaka, T. Synlett 1999, 705-708
22. Linghu, X.; Potnick, J. R.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 3070-3071
23. Nahm, M. R.; Linghu, X.; Potnick, J. R.; Yates, C. M.; White, P. S.; Johnson, J. S. Angew. Chem., Int. Ed. 2005, 44, 2377-2379
24. Garrett, M. R.; Tarr, J. C.; Johnson, J. S. J. Am. Chem. Soc. 2007, 129, 12944-12945
25. Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314-2315
26. Mattson, A. E.; Scheidt, K. A. Org. Lett. 2004, 6, 4363-4366
27. Mattson, A. E.; Bharadwaj, A. R.; Zuhl, A. M.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 71, 5715-5724
28. Sekiguchi, A.; Kabe, Y.; Ando, W. Tetrahedron Lett. 1979, 871-872
29. Sekiguchi, A.; Kabe, Y.; Ando, W. J. Org. Chem. 1982, 47, 2900-2903
30. Sekiguchi, A.; Ando, W. J. Chem. Soc., Chem. Commun. 1979, 575-576
31. Bolm, C.; Kasyan, A.; Heider, P.; Saladin, S.; Drauz, K.; Guenther, K.; Wagner, C. Org. Lett. 2002, 4, 2265-2267
32. Yao, W.; Wang, J. Org. Lett. 2003, 5, 1527-1530
33. Darkins, P.; McCarthy, N.; Anthony, M.; McKervey; O'Donnell, K.; Ye, T.; Walker, B. Tetrahedron: Asymmetry 1994, 5, 195-198
34. Nicewicz, D. A.; Brétéché, G.; Johnson, J. S. Org. Synth. 2008, 85, 278-286
35. Sugimura, H.; Watanabe, T. Synlett 1994, 175-177
36. DiMauro, E. F.; Kozlowski, M. C. J. Am. Chem. Soc. 2002, 124, 12668-12669
37. Frantz, D. E.; Faessler, R.; Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245-11246
38. Nicewicz, D. A.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 6170-6171
39. Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687-9688
40. Masuyama, Y.; Tsunoda, T.; Kurusu, Y. Chem. Lett. 1989, 18, 1647-1650
41. Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699
42. Linghu, X.; Johnson, J. S. Unpublished results. Our original publication showed -78 °C as the reaction temperature in the graphic but did not indicate that the reaction was warmed to 0 °C prior to the quench. (The experimental procedure was detailed in the Supporting Information accompanying that paper.) Unbeknownst to us at the time, this method was very effective for giving the thermodynamic isomer. The kinetic aldolization was discovered subsequently.
43. McFarland, C. M.; McIntosh, M. C. The Ireland-Claisen Rearrangement (1972-2004). In The Claisen Rearrangement: Methods and Applications; Hiersemann, M.; Nubbemeyer, U., Eds.; Wiley-VCH: Weinheim, 2007; pp 117-210.
44. Schmitt, D. C.; Johnson, J. S. Org. Lett. 2010, 12, 944-947
45. Dekker, J.; Budzelaar, P. H. M.; Boersma, J.; Van der Kerk, G. J. M.; Spek, A. J. Organometallics 1984, 3, 1403-1407
46. Hurley, E. R.; He, X.; Brown, S. N.; Henderson, K. W. J. Am. Chem. Soc. 2009, 131, 6056-6057
47. Greszler, S. N.; Johnson, J. S. Angew. Chem., Int. Ed. 2009, 48, 3689-3691
48. Lettan, R. B.; Galliford, C. V.; Woodward, C. C.; Scheidt, K. A. J. Am. Chem. Soc. 2009, 131, 8805-8814
49. Yao, M.; Lu, C.-D. Org. Lett. 2011, 13, 2782-2785
50. Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708-709
51. Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423-1424
52. Kuwajima, I.; Kato, M. Tetrahedron Lett. 1980, 21, 623-626
53. Enda, J.; Matsutani, T.; Kuwajima, I. Tetrahedron Lett. 1984, 25, 5307-5310
54. Kato, M.; Mori, A.; Oshino, H.; Enda, J.; Kobayashi, K.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 1773-1778
55. Enda, J.; Kuwajima, I. J. Am. Chem. Soc. 1985, 107, 5495-5501
56. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302
57. Boyce, G. R.; Johnson, J. S. Angew. Chem., Int. Ed. 2010, 49, 8930-8933
58. Luzzio, F. A. Tetrahedron 2001, 57, 915-945
59. Al-Rashid, Z. F.; Johnson, W. L.; Hsung, R. P.; Wei, Y.; Yao, P.-Y.; Liu, R.; Zhao, K. J. Org. Chem. 2008, 73, 8780-8784
60. Boyce, G. R.; Liu, S.; Johnson, J. S. Org. Lett. 2012, 14, 652-655
61. Plietker, B. J. Org. Chem. 2004, 69, 8287-8296
62. Linghu, X.; Satterfield, A. D.; Johnson, J. S. J. Am. Chem. Soc. 2006, 128, 9302-9303
63. Greszler, S. N.; Johnson, J. S. Org. Lett. 2009, 11, 827-830
64. Kinnaird, J. W. A.; Ng, P. Y.; Kubota, K.; Wang, X.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7920-7921
65. Steward, K. M.; Johnson, J. S. Org. Lett. 2010, 12, 2864-2867
66. Greszler, S. N.; Malinowski, J. T.; Johnson, J. S. J. Am. Chem. Soc. 2010, 132, 17393-17395
67. Greszler, S. N.; Malinowski, J. T.; Johnson, J. S. Org. Lett. 2011, 13, 3206-3209
68. Kohama, T.; Enokita, R.; Okazaki, T.; Miyaoka, H.; Torikata, A.; Inukai, M.; Kaneko, I.; Kagasaki, T.; Sakaida, Y.; Satoh, A.; Shirashi, A. J. Antibiot. 1993, 46, 1503
69. Kohama, T.; Nakamura, T.; Kinoshita, T.; Kaneko, I.; Shiraishi, A. J. Antibiot. 1993, 46, 1512
70. Matsuhashi, H.; Shimada, K. Tetrahedron 2002, 58, 5619
71. Shimada, K.; Kaburagi, Y.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 4048
72. Miyashita, K.; Tsunemi, T.; Hosokawa, T.; Ikejiri, M.; Imanishi, T. Tetrahedron Lett. 2007, 48, 3829
73. Miyashita, K.; Tsunemi, T.; Hosokawa, T.; Ikejiri, M.; Imanishi, T. J. Org. Chem. 2008, 73, 5360
74. Moise, J.; Sonowane, R. P.; Corsi, C.; Wendeborn, S. V.; Arseniyadis, S.; Cossy, J. Synlett 2008, 2617
75. Fushimi, S.; Nishikawa, S.; Shimazo, A.; Seto, H. J. Antibiot. 1989, 42, 1019
76. Fushimi, S.; Furihata, K.; Seto, H. J. Antibiot. 1989, 42, 1026
77. Ozasa, T.; Suzuki, K.; Sasamata, M.; Tanaka, K.; Koburi, M.; Kadota, S.; Nagai, K.; Saito, T.; Watanabe, S.; Iwanami, M. J. Antibiot. 1989, 42, 1331
78. Ozasa, T.; Tanaka, K.; Sasamata, M.; Kaniwa, H.; Shimizu, M.; Matsumoto, H.; Iwanami, M. J. Antibiot. 1989, 42, 1339
79. Shibata, T.; Kurihara, S.; Yoda, K.; Haruyama, H. Tetrahedron 1995, 51, 11999
80. Sekiyama, Y.; Palaniappan, N.; Reynolds, K. A.; Osada, H. Tetrahedron 2003, 59, 7465
81. Choudhuri, S. D.; Ayers, S.; Soine, W. H.; Reynolds, K. A. J. Antibiot. 2005, 58, 573
82. Mizuhara, N.; Usuki, Y.; Ogita, M.; Fujita, K.; Kuroda, M.; Doe, M.; Lio, H.; Tanaka, T. J. Antibiot. 2007, 60, 762
83. Wang, Y.-G.; Takeyama, T.; Kobayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 3320
84. Nonaka, H.; Maeda, N.; Kobayashi, Y. Tetrahedron Lett. 2007, 48, 5601
85. Shibahara, S.; Fujina, M.; Tashiro, Y.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Org. Lett. 2008, 10, 2139
86. Druais, V.; Hall, M. J.; Corsi, C.; Wendeborn, S. V.; Meyer, C.; Cossy, J. Org. Lett. 2009, 11, 935
87. Konig, C. M.; Gebhardt, B.; Schleth, C.; Dauber, M.; Koert, U. Org. Lett. 2009, 11, 2728
88. Shibahara, S.; Fujino, M.; Tashiro, Y.; Nanako, O.; Esumi, T.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Synthesis 2009, 2935
89. Gebhardt, B.; König, C. M.; Schleth, C.; Dauber, M.; Koert, U. Chem.-Eur. J. 2010, 16, 5934-5941
90. Evans, D. A.; Ennis, M. D.; Le, T.; Mandel, N.; Mandel, G. J. Am. Chem. Soc. 1984, 106, 1154
91. Tanabe, Y.; Hamasaki, R.; Funakoshi, S. Chem. Commun. 2001, 1674
92. Iida, A.; Nakazawa, S.; Okabayshi, T.; Horii, A.; Misaki, T.; Tanabe, Y. Org. Lett. 2006, 8, 5215
93. Mermerian, A.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 5604
94. Shen, X.; Wasmuth, A. S.; Zhao, J.; Zhu, C.; Nelson, S. G. J. Am. Chem. Soc. 2006, 128, 7438
95. Green, M. E.; Rech, J. C.; Floreancig, P. E. Angew. Chem., Int. Ed. 2008, 47, 7317
96. Shimizu, M.; Ishii, K.; Fujisawa, T. Chem. Lett. 1997, 765
97. For a review of reactivity, see: Wang, Y.; Tennyson, R. L.; Romo, D. Heterocycles 2004, 64, 605
98. Iida, A.; Takai, K.; Okabayashi, T.; Misaki, T.; Tanabe, Y. Chem. Commun. 2005, 3171
99. Hauser, C. R.; Renfrow, W. B. J. Am. Chem. Soc. 1937, 59, 1823
100. Yatluk, Y. G.; Chernyak, S. V.; Suvorov, A. L.; Khrustaleva, E. A.; Abramova, V. I. Russ. J. Gen. Chem. 2001, 71, 965
101. Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742-9743
102. Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem. Lett. 1987, 1923-1926
103. Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, E.; Kumar, K. V. P. P. Chem. Rev. 2009, 109, 2551-2651
104. Schmitt, D. C.; Lam, L.; Johnson, J. S. Org. Lett. 2011, 13, 5136-5139
105. Shiozawa, H.; Takahashi, M.; Takatsu, T.; Kinoshita, T.; Tanzawa, K.; Hosoya, T.; Furuya, K.; Takahashi, S.; Furihata, K.; Seto, H. J. Antibiot. 1995, 48, 357-362
106. Morokuma, K.; Taira, Y.; Uehara, Y.; Shibahara, S.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2008, 49, 6043-6045
107. Calo, F.; Richardson, J.; White, A. J. P.; Barrett, A. G. M. Tetrahedron Lett. 2009, 50, 1566-1567
108. Zammit, S. C.; White, J. M.; Rizzacasa, M. A. Org. Biomol. Chem. 2005, 3, 2073-207
109. Zammit, S. C.; Ferro, V.; Hammond, E.; Rizzacasa, M. A. Org. Biomol. Chem. 2007, 5, 2826-2834
110. Hirai, K.; Ooi, H.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2003, 5, 857-859
111. Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826
112. Hosomi, A.; Shoji, H.; Sakurai, H. Chem. Lett. 1985, 14, 1049-1052
113. Burkhard, J. A.; Tchitchanov, B. H.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 5379-5382
114. Noji, M.; Sunahara, H.; Tsuchiya, K.-i.; Mukai, T.; Komasaka, A.; Ishii, K. Synthesis 2008, 3835-3845
115. Nicewicz, D. A.; Satterfield, A. D.; Schmitt, D. C.; Johnson, J. S. J. Am. Chem. Soc. 2008, 130, 17281-17283
116. Dawson, M. J.; Farthing, J. E.; Marshall, P. S.; Middleton, R. F.; Oneill, M. J.; Shuttleworth, A.; Stylli, C.; Tait, R. M.; Taylor, P. M.; Wildman, H. G.; Buss, A. D.; Langley, D.; Hayes, M. V. J. Antibiot. 1992, 45, 639-647
117. Bergstrom, J. D.; Kurtz, M. M.; Rew, D. J.; Amend, A. M.; Karkas, J. D.; Bostedor, R. G.; Bansal, V. S.; Dufresne, C.; VanMiddlesworth, F. L.; Hensens, O. D. Proc. Nat. Acad. Sci. U.S.A. 1993, 90, 80-84
118. Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1994, 116, 10825-6
119. Carreira, E. M.; Du Bois, J. J. Am. Chem. Soc. 1995, 117, 8106-25
120. Nicolaou, K. C.; Yue, E. W.; Naniwa, Y.; De Riccardis, F.; Nadin, A.; Leresche, J. E.; La Greca, S.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2184-2187
121. Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; La Greca, S.; Tsuri, T.; Yue, E. W.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 2187-2190
122. Nicolaou, K. C.; Nadin, A.; Leresche, J. E.; Yue, E. W.; La Greca, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 2190-2191
123. Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem.-Eur. J. 1995, 1, 467-94
124. Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111-12
125. Stoermer, D.; Caron, S.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9115-9125
126. Caron, S.; Stoermer, D.; Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1996, 61, 9126-9134
127. Sato, H.; Nakamura, S.; Watanabe, N.; Hashimoto, S. Synlett 1997, 451-454
128. Nakamura, S.; Sato, H.; Hirata, Y.; Watanabe, N.; Hashimoto, S. Tetrahedron 2005, 61, 11078-11106
129. Armstrong, A.; Jones, L. H.; Barsanti, P. A. Tetrahedron Lett. 1998, 39, 3337-3340
130. Armstrong, A.; Barsanti, P. A.; Jones, L. H.; Ahmed, G. J. Org. Chem. 2000, 65, 7020-7032
131. Tomooka, K.; Kikuchi, M.; Igawa, K.; Suzuki, M.; Keong, P.-H.; Nakai, T. Angew. Chem., Int. Ed. 2000, 39, 4502-4505
132. Freeman-Cook, K. D.; Halcomb, R. L. J. Org. Chem. 2000, 65, 6153-6159
133. Nakamura, S.; Hirata, Y.; Kurosaki, T.; Anada, M.; Kataoka, O.; Kitagaki, S.; Hashimoto, S. Angew. Chem., Int. Ed. 2003, 42, 5351-5355
134. Hirata, Y.; Nakamura, S.; Watanabe, N.; Kataoka, O.; Kurosaki, T.; Anada, M.; Kitagaki, S.; Shiro, M.; Hashimoto, S. Chem.-Eur. J. 2006, 12, 8898-8925
135. Bunte, J. O.; Cuzzupe, A. N.; Daly, A. M.; Rizzacasa, M. A. Angew. Chem., Int. Ed. 2006, 45, 6376-6380
136. Wang, Y. Z.; Metz, P. Chem.-Eur. J. 2011, 17, 3335-3337
137. Nadin, A.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1622-1656
138. Jotterand, N.; Vogel, P. Curr. Org. Chem. 2001, 5, 637-661
139. Armstrong, A.; Blench, T. J. Tetrahedron 2002, 58, 9321-9349
140. Hendrickson, J. B. Top. Curr. Chem. 1976, 62, 49-172
141. Hendrickson, J. B. J. Am. Chem. Soc. 1977, 99, 5439-5450
142. Burns, N.; Baran, P.; Hoffmann, R. Angew. Chem., Int. Ed. 2009, 48, 2854-2867
143. Radosevich, A. T.; Musich, C.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 1090-1091
144. White, J. D.; Cutshall, N. S.; Kim, T. S.; Shin, H. J. Am. Chem. Soc. 1995, 117, 9780-9781