Tris(4-anisyl)phosphine as an Efficient and Practical Reagent for the Synthesis of (E)-2-Benzylidenesuccinates
Wei Wang
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, China
Search for more papers by this authorWeibing Liu
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, China
Search for more papers by this authorChunli Qiao
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, China
Search for more papers by this authorWei Wang
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, China
Search for more papers by this authorWeibing Liu
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, China
Search for more papers by this authorChunli Qiao
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, China
Search for more papers by this authorAbstract
Condensation of maleic anhydride or dimethyl maleate with benzylaldehydes controlled by tris(4-anisyl)-phosphine to synthesize dimethyl (E)-2-benzylidenesuccinates has been systematically investigated. The protocol gives the product with high stereoselectivity in moderate to good yields under mild conditions. A plausible mechanism has been proposed.
REFERENCES
- 1a Wittig, G.; Schöllkopf, U.. Ber. Bunsen-Ges. Phys. Chem., 1954, 87, 1318.
- 1b Christopher, J. O.; Jennifer, L.. Angew. Chem., Int. Ed., 2009, 48, 6836.
- 1c McNulty, J.; Das, P.. Tetrahedron Lett., 2009, 50, 5737.
- 2a Horner, L.. Chem. Ber., 1959, 92, 1499.
- 2b Chen, Z. B.; Shou, W. G.; Wang, Y. G.. Synthesis, 2009, 1075.
- 3a Wadsworth, W. S.; Emmons, W. D.. J. Am. Chem. Soc., 1961, 83, 1733.
- 3b Wang, X. Q.; He, F. K.. Chin. J. Chem., 2003, 21, 805.
- 3c Elise, C.; Isabelle, G.. Synlett, 2009, 263.
- 4a Bilenko, V.; Jiao, H. J.; Spannenberg, A.; Fischer, C.. Eur. J. Org. Chem., 2007, 758.
- 4b Liu, Y.; Sandoval, C. A.; Yamaguchi, Y. I.; Zhang, X.; Wang, Z.; Kato, K.; Ding, K. L.. J. Am. Chem. Soc., 2006, 128, 14212.
- 4c Kapferer, T.; Brueckner, R.. Eur. J. Org. Chem., 2006, 2119.
- 4d Boaz, N. W.; Mackenzie, E. B.; Debenham, S. D.; Large, S. E.. J. Org. Chem., 2005, 70, 1872.
- 4e Korostylev, A.; Selent, D.; Monsees, A.. Tetrahedron: Asymmetry, 2003, 14, 1905.
- 4f Boaz, N. W.; Debenham, S. D.; Mackenzie, E. B.; Large, S. E.. Org. Lett., 2002, 4, 2421.
- 4g Suprakas, S. R.; Mamookho, E. M.. Polymer, 2009, 50, 4635.
- 5a Hiroshi, S.; Tsuyoshi, Q.; Hiroshi, Q.; Akio, Q.. Chem. Pharm. Bull., 2006, 54, 1686.
- 5b Momose, T. F.; Tanabe, G.; Tsujimori, H. K.; Muraoka, O.. Chem. Pharm. Bull., 1992, 40, 2525.
- 6a Johnson, W. S.; Daub, G. H.. Org. React., 1953, 6, 1.
- 6b Gordaliza, M.; Migueldel, J. M.; Corral, M. A.; Castro, M. A.; Salinero, A.. Synlett, 1996, 1201.
- 6c Cameron, A. F.; Duncanson, F. D.; Freer, A. A.; Armstrong, D. W.; Ramage, R.. J. Chem. Soc., Perkin Trans. 2, 1975, 1030.
- 6d Linke, S.; Kurz, J.; Lipinski, D.; Gau, W.. Liebigs Ann. Chem., 1980, 542.
- 7a Hiroshi, S.; Tsuyoshi, O.; Hiroshi, O.; Akio, O.. Chem. Pharm. Bull., 2006, 54, 1686.
- 7b Ding, H. F.; Cheng, M.. Org. Lett., 2005, 7, 2125.
- 7c Donate, P. M.; Jimenez, R. R., BR 2004003135, 2006. Chem. Abstr., 2006, 146, 358685.
- 7d Shen, Y. C.; Zhang, Z. H.. J. Chem. Res., Synop., 1998, 10, 642.
- 7e Hideya, M.. Tetrahedron, 2006, 62, 8539.
- 7f McComble, S. W.; Luchaco, C. A.. Tetrahedron Lett., 1997, 33, 5775.
