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http://dx.doi.org/10.5012/bkcs.2005.26.10.1481

Baylis-Hillman Reaction and Chemical Transformations of Baylis-Hillman Adducts  

Lee, Ka-Young (Department of Chemistry and Institute of Basic Science, Chonnam National University)
Gowrisankar, Saravanan (Department of Chemistry and Institute of Basic Science, Chonnam National University)
Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
Publication Information
Bulletin of the Korean Chemical Society / v.26, no.10, 2005 , pp. 1481-1490 More about this Journal
Abstract
Carbon-carbon single bond-forming reaction is the most useful and fundamental reaction in organic synthesis. Most of the basic carbon-carbon single bond-forming reactions, thus, developed in the past. In these respects, conceptually new C-C bond formation reaction can be highlighted. The Baylis-Hillman reaction was found at the early 1970’s. However, extensive studies on this highly potential reaction were started only before 15 years. This review has been written to shed more lights to the importance of Baylis-Hillman reaction. We have focused mainly on the reaction mechanism, conceptually related reactions, and chemical transformations of the Baylis-Hillman adducts.
Keywords
Baylis-Hillman reaction; Baylis-Hillman adducts; Chemical transformations;
Citations & Related Records
Times Cited By KSCI : 9  (Citation Analysis)
Times Cited By Web Of Science : 127  (Related Records In Web of Science)
Times Cited By SCOPUS : 1
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1 Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627   DOI   ScienceOn
2 Rauhut, M.; Currier, H. U. S. Patent 3,074,999, 1963
3 Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815   DOI
4 Baylis, A. B.; Hillman, M. E. D. German Patent 2,155,113, 1972
5 Jellerichs, B. G.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758   DOI   ScienceOn
6 Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811   DOI   ScienceOn
7 Wang, L.-C.; Luis, A. L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402   DOI   ScienceOn
8 Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682   DOI   ScienceOn
9 Luis, A. L.; Krische, M. J. Synthesis 2004, 2579
10 Cho, C.-W.; Kong, J.-R.; Krische, M. J. Org. Lett. 2004, 6, 1337   DOI   ScienceOn
11 Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404   DOI   ScienceOn
12 Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035   DOI   ScienceOn
13 Roth, F.; Gygax, P.; Frater, G. Tetrahedron Lett. 1992, 33, 1045   DOI   ScienceOn
14 Dinon, F.; Richards, E.; Murphy, P. J.; Hibbs, D. E.; Hursthouse, M. B.; Malik, K. M. A. Tetrahedron Lett. 1999, 40, 3279   DOI   ScienceOn
15 Richards, E.; Murphy, P. J.; Dinon, F.; Fratucello, S.; Brown, P. M.; Gelbrich, T.; Hursthouse, M. B. Tetrahedron 2001, 57, 7771   DOI   ScienceOn
16 Brown, P. M.; Kappel, N.; Murphy, P. J. Tetrahedron Lett. 2002, 43, 8707   DOI   ScienceOn
17 Yeo, J. E.; Yang, X.; Kim, H. J.; Koo, S. Chem. Commun. 2004, 236
18 Hoffmann, H. M. R.; Rabe, J. Angew. Chem. Int. Ed. Engl. 1983, 22, 795   DOI
19 Hill, J. S.; Isaacs, N. S. J. Phys. Org. Chem. 1990, 3, 285   DOI
20 Hill, J. S.; Isaacs, N. S. Tetrahedron Lett. 1986, 27, 5007   DOI   ScienceOn
21 Price, K. E.; Broadwater, S. J.; Jung, H. M.; McQuade, D. T. Org. Lett. 2005, 7, 147   DOI   ScienceOn
22 Price, K. E.; Broadwater, S. J.; Walker, B. J.; McQuade, D. T. J. Org. Chem. 2005, 70, 3980   DOI   ScienceOn
23 Ciganek, E., In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 51, pp 201-350
24 Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001   DOI   ScienceOn
25 Kim, J. N.; Kim, H. S.; Gong, J. H.; Chung, Y. M. Tetrahedron Lett. 2001, 42, 8341   DOI   ScienceOn
26 Im, Y. J.; Chung, Y. M.; Gong, J. H.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 787   DOI   ScienceOn
27 Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209   DOI   ScienceOn
28 Shanmugam, P.; Rajasingh, P. Tetrahedron 2004, 60, 9283   DOI   ScienceOn
29 Im, Y. J.; Lee, K. Y.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2002, 43, 4675   DOI   ScienceOn
30 Shanmugam, P.; Rajasingh, P. Synlett 2005, 939
31 Paquette, L. A.; Mendez-Andino, J. Tetrahedron Lett. 1999, 40, 4301   DOI   ScienceOn
32 Shanmugam, P.; Rajasingh, P. Tetrahedron Lett. 2005, 46, 3369   DOI   ScienceOn
33 Lee, H. J.; Seong, M. R.; Kim, J. N. Tetrahedron Lett. 1998, 39, 6223   DOI   ScienceOn
34 Gowrisankar, S.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2005, 46, 4859   DOI   ScienceOn
35 Methot, J. L.; Roush, W. R. Org. Lett. 2003, 5, 4223   DOI   ScienceOn
36 Mergott, D. J.; Frank, S. A.; Roush, W. R. Org. Lett. 2002, 4, 3157   DOI   ScienceOn
37 Declerck, V.; Ribiere, P.; Martinez, J.; Lamaty, F. J. Org. Chem. 2004, 69, 8372   DOI   ScienceOn
38 Krishna, P. R.; Narsingam, M.; Kannan, V. Tetrahedron Lett. 2004, 45, 4773   DOI   ScienceOn
39 Shanmugam, P.; Rajasingh, P. Chem. Lett. 2002, 1212
40 Basavaiah, D.; Bakthadoss, M.; Pandiaraju, S. Chem. Commun. 1998, 1639
41 Anand, R. V.; Baktharaman, S.; Singh, V. K. Tetrahedron Lett. 2002, 43, 5393   DOI   ScienceOn
42 Basavaiah, D.; Pandiaraju, S.; Padmaja, K. Synlett 1996, 393
43 Basavaiah, D.; Mallikarjuna Reddy, R. Tetrahedron Lett. 2001, 42, 3025   DOI   ScienceOn
44 Basavaiah, D.; Krishnamacharyulu, M.; Suguna Hyma, R.; Pandiaraju, S. Tetrahedron Lett. 1997, 38, 2141   DOI   ScienceOn
45 Basavaiah, D.; Bakthadoss, M.; Jayapal Reddy, G. Synthesis 2001, 919
46 Lee, H. J.; Kim, T. H.; Kim, J. N. Bull. Korean Chem. Soc. 2001, 22, 1063
47 Gowrisankar, S.; Lee, K. Y.; Lee, C. G.; Kim, J. N. Tetrahedron Lett. 2004, 45, 6141   DOI   ScienceOn
48 Kim, J. N.; Lee, H. J.; Lee, K. Y.; Kim, H. S. Tetrahedron Lett. 2001, 42, 3737   DOI   ScienceOn
49 Chung, Y. M.; Lee, H. J.; Hwang, S. S.; Kim, J. N. Bull. Korean Chem. Soc. 2001, 22, 799
50 Chamakh, A.; Amri, H. Tetrahedron Lett. 1998, 39, 375   DOI   ScienceOn
51 Chamakh, A.; M'hirsi, M.; Villieras, J.; Lebreton, J.; Amri, H. Synthesis 2000, 295
52 Kim, J. N.; Im, Y. J.; Kim, J. M. Tetrahedron Lett. 2002, 43, 6597   DOI   ScienceOn
53 Kim, J. N.; Kim, J. M.; Lee, K. Y. Synlett 2003, 821
54 Im, Y. J.; Lee, C. G.; Kim, H. R.; Kim, J. N. Tetrahedron Lett. 2003, 44, 2987   DOI   ScienceOn
55 Basavaiah, D.; Rao, J. S.; Reddy, R. J. J. Org. Chem. 2004, 69, 7379   DOI   ScienceOn
56 Kim, J. N.; Kim, J. M.; Lee, K. Y.; Gowrisankar, S. Bull. Korean Chem. Soc. 2004, 25, 1733   DOI   ScienceOn
57 Kim, J. M.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2004, 25, 328   DOI   ScienceOn
58 Familoni, O. B.; Kaye, P. T.; Klass, P. J. Chem. Commun. 1998, 2563
59 Lee, K. Y.; Kim, J. M.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 1493   DOI   ScienceOn
60 Kim, J. M.; Lee, K. Y.; Lee, S.; Kim, J. N. Tetrahedron Lett. 2004, 45, 2805   DOI   ScienceOn
61 Lee, K. Y.; Na, J. E.; Lee, J. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2004, 25, 1280   DOI   ScienceOn
62 Lee, M. J.; Lee, K. Y.; Lee, J. Y.; Kim, J. N. Org. Lett. 2004, 6, 3313   DOI   ScienceOn
63 Gong, J. H.; Im, Y. J.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2002, 43, 1247   DOI   ScienceOn
64 Kim, J. N.; Im, Y. J.; Gong, J. H.; Lee, K. Y. Tetrahedron Lett. 2001, 42, 4195   DOI   ScienceOn
65 Rauhut, M.; Currier, H. Chem. Abstr. 1963, 58, 11224a
66 Baylis, A. B.; Hillman, M. E. D. Chem. Abstr. 1972, 77, 34174q
67 Lee, M. J.; Lee, K. Y.; Park, D. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1281   DOI   ScienceOn
68 Gowrisankar, S.; Lee, M. J.; Lee, S.; Kim, J. N. Bull. Korean Chem. Soc. 2004, 25, 1963   DOI   ScienceOn
69 Gowrisankar, S.; Lee, C. G.; Kim, J. N. Tetrahedron Lett. 2004, 45, 6949   DOI   ScienceOn
70 Kim, J. N.; Lee, K. Y.; Kim, H. S.; Kim, T. Y. Org. Lett. 2000, 2, 343   DOI   ScienceOn
71 Basavaiah, D.; Pandiaraju, S.; Krishnamacharyulu, M. Synlett 1996, 747
72 Lee, C. G.; Lee, K. Y.; Lee, S.; Kim, J. N. Tetrahedron 2005, 61, 1493   DOI   ScienceOn
73 Kim, S. C.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1001   DOI   ScienceOn
74 Basavaiah, D.; Rao, J. S. Tetrahedron Lett. 2004, 45, 1621   DOI   ScienceOn
75 Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 939   DOI   ScienceOn
76 Basavaiah, D.; Mallikarjuna Reddy, R. M.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron 2002, 58, 3693   DOI   ScienceOn
77 O'Dell, D. K.; Nicholas, K. M. J. Org. Chem. 2003, 68, 6427   DOI   ScienceOn
78 Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron 2003, 59, 385   DOI   ScienceOn