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http://dx.doi.org/10.5012/bkcs.2010.31.03.645

Efficient Synthetic Method of Z-Selective 2-Halo-1,3-dienes from Reactions of Allenols Possessing Ethoxycarbonyl and Vinyl Group with Indium Trihalide  

Eom, Da-Han (Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University)
Kim, Sung-Hong (Analysis Research Division Daegu Center, Korea Basic Science Institute)
Lee, Phil-Ho (Department of Chemistry and Institute for Molecular Science and Fusion Technology, Kangwon National University)
Publication Information
Abstract
An efficient synthetic method of Z-selective 3-ethoxycarbonyl-2-halo-1,3-dienes and 3-vinyl-2-halo-1,3-dienes was developed from the reaction of allenols having ethoxycarbonyl and vinyl group with indium trihalides at room temperature in $CH_2Cl_2$.
Keywords
Allenol; 2-Halo-1,3-diene; Indium trihalide; Selectivity;
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1 Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, U.K., 1990.
2 Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 315.
3 Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179.   DOI   ScienceOn
4 Marsault, E.; Toro, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243.   DOI   ScienceOn
5 Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668.   DOI   ScienceOn
6 Horvath, A.; Backvall, J.-E. J. Org. Chem. 2001, 66, 8120.   DOI   ScienceOn
7 Ma, S.; Wang, G. Tetrahedron Lett. 2002, 43, 5723.   DOI   ScienceOn
8 Deng, Y.; Jin, X.; Ma, S. J. Org. Chem. 2007, 72, 5901.   DOI   ScienceOn
9 Seomoon, D.; A. J.; Lee, P. H. Org. Lett. 2009, 11, 2401.   DOI   ScienceOn
10 Lee, J.-Y.; Lee, P. H. J. Org. Chem. 2008, 73, 7413.   DOI   ScienceOn
11 Lee, K.; Lee, P. H. Org. Lett. 2008, 10, 2441.   DOI   ScienceOn
12 Lee, K.; Lee, P. H. Tetrahedron Lett. 2008, 49, 4302.   DOI   ScienceOn
13 Lee, W.; Kang, Y.; Lee, P. H. J. Org. Chem. 2008, 73, 4326.   DOI   ScienceOn
14 Seomoon, D.; Lee, P. H. J. Org. Chem. 2008, 73, 1165.   DOI   ScienceOn
15 Lee, K.; Lee, P. H. Bull. Korean Chem. Soc. 2008, 29, 487.   DOI   ScienceOn
16 Lee, J.-Y.; Lee, P. H. Bull. Korean Chem. Soc. 2007, 28, 1929.   DOI   ScienceOn
17 Lee, P. H. Bull. Korean Chem. Soc. 2007, 28, 17.   DOI   ScienceOn
18 Seomoon, D.; Lee, K.; Kim, H.; Lee, P. H. Chem. Eur. J. 2007, 13, 5197.   DOI   ScienceOn
19 Lee, P. H.; Lee, K.; Kang, Y. J. Am. Chem. Soc. 2006, 128, 1139.   DOI   ScienceOn
20 A, J.; Lee, P. H. Bull. Korean Chem. Soc. 2009, 30, 471.   DOI   ScienceOn
21 Clardy, J.; Forsyth, C. J. J. Am. Chem. Soc. 1990, 112, 3497.   DOI
22 Hamze, A.; Provot, O.; Brion, J.-D.; Alami, M. J. Org. Chem. 2007, 72, 3868.   DOI   ScienceOn
23 Lee, K.; Lee, P. H. Chem. Eur. J. 2007, 13, 8877.   DOI   ScienceOn
24 Deng, Y.; Jin, X.; Fu, C.; Ma, S. Org. Lett. 2009, 11, 2169.   DOI   ScienceOn
25 Cho, Y. S.; Jun. B. K.; Pae, A. N.; Cha, J. H.; Koh, H. Y.; Chang, M. H.; Han, S-Y. Synthesis 2004, 16, 2620.
26 Park, C.; Lee, P. H. Org. Lett. 2008, 10, 3359.   DOI   ScienceOn
27 Yu, H.; Lee, P. H. J. Org. Chem. 2008, 73, 5183.   DOI   ScienceOn
28 Lee, P. H.; Lee, K.; Sung, S.-Y.; Chang, S. J. Org. Chem. 2001, 66, 8846.
29 Park, J.; Kim, S. H.; Lee, P. H. Org. Lett. 2008, 10, 5067.   DOI   ScienceOn
30 Choe, Y.; Lee, P. H. Org. Lett. 2009, 11, 1445.   DOI   ScienceOn