SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 07: 1159 - 1168

DOI: https://doi.org/10.6023/cjoc201205003

ACCOUNT

Studies on Reactivity of in situ Generated Allylic Phosphorus Ylides with Aldehydes

  • Xu Silong ,
  • He Zhengjie
Expand
  • State Key Laboratory of Elemento-Organic Chemistry and Department of Chemistry, Nankai University, Tianjin 300071

Received date: 2012-05-03

  Revised date: 2012-05-19

  Online published: 2012-05-23

Supported by

Project Supported by the National Natural Science Foundation of China (Nos. 20872063, 21072100) and the Research Fund for the Doctoral Program of Higher Education of China (No. 20110031110012).

Fold

Abstract

This account primarily summarizes our recent work on the reactivity of in situ generated allylic phosphorus ylides with aldehydes. Under the mediation of stoichiometric tertiary phosphines, allylic carbonates or allenoates readily undergo highly stereoselective three-component Wittig and vinylogous Wittig olefination reactions through in situ generated allylic phosphorus ylides. These reactions constitute simple and efficient synthetic methods for polysubstituted 1,3-dienes. Under the catalysis of tertiary phosphines, γ-methyl allenoates chemoselectively undertake several annulations with aldehydes via a key intermediate of allylic phosphorus ylide, providing atom economical synthesis of 5- and 6-membered oxygen heterocycles. By experimental approaches such as deuterium-labeling and NMR monitoring, mechanisms of the above mentioned reactions have also been investigated.

Key words： phosphorus ylide; Wittig reaction; vinylogous Wittig reaction; annulation reaction

Cite this article

Xu Silong , He Zhengjie . Studies on Reactivity of in situ Generated Allylic Phosphorus Ylides with Aldehydes[J]. Chinese Journal of Organic Chemistry, 2012 , 32(07) : 1159 -1168 . DOI: 10.6023/cjoc201205003

References

1 Kolodiazhnyi, O. I. Phosphorus Ylides: Chemistry and Application in Organic Synthesis, Wiley-VCH, New York, 1999.
2 Maryanoff, B. E.; Reitz, A. B., Chem. Rev. 1989, 89, 863.  
3 Nicolaou, K. C.; Hrter, M. W.; Gunzner, J. L.; Nadin, A., Liebigs Ann. Recl. 1997, 1997, 1283.  
4 Riches, S. L.; Saha, C.; Filgueira, N. F. N.; Grange, E.; McGarrigle, E. M.; Aggarwal, V. K., J. Am. Chem. Soc. 2010, 132, 7626.  
5 (a) Tamura, R.; Saegusa, K.; Kakihana, M.; Oda, D., J. Org. Chem.1988, 53, 2723; (b) Wang, Q.; El Khoury, M.; Schlosser, M., Chem-Eur. J. 2000, 6, 420; (c) Robiette, R.; Richardson, J.; Aggarwal, V. K.; Harvey, J. N., J. Am. Chem. Soc. 2006, 128, 2394.  
6 (a) Methot, J. L.; Roush, W. R., Adv. Synth. Catal. 2004, 346, 1035; (b) Cowen, B. J.; Miller, S. J., Chem. Soc. Rev. 2009, 38, 3102; (c) Lu, X.; Zhang, C.; Xu, Z., Acc. Chem. Res. 2001, 34, 535; (d) Wei, Y.; Shi, M., Acc. Chem. Res. 2010, 43, 1005; (e) Ye, L.-W.; Zhou, J.; Tang, Y., Chem. Soc. Rev. 2008, 37, 1140; (f) Nair, V.; Menon, R. S.; Sreekanth, A. R.; Abhilash, N.; Biju, A. T., Acc. Chem. Res. 2006, 39, 520; (g) Zhao, Q.-Y.; Lian, Z.; Wei, Y.; Shi, M., Chem. Commun. 2012, 48,1724.  
7 (a) Oda, R.; Kawabata, T.; Tanimoto, S., Tetrahedron Lett. 1964, 5,1653; (b) McClure, J. D., Tetrahedron Lett. 1967, 8, 2401; (c) Hedaya, E.; Theodoropulos, S., Tetrahedron 1968, 24, 2241; (d) McCombie, S. W.; Luchaco, C. A., Tetrahedron Lett. 1997, 38, 5775; (e) Heys, L.; Murphy, P. J.; Coles, S. J.; Gelbrich, T.; Hursthouse, M. B., Tetrahedron Lett. 1999, 40, 7151; (f) Low, K. H.; Magomedov, N. A., Org. Lett. 2005, 7, 2003.  
8 Basavaiah, D.; Reddy, B. S.; Badsara, S. S., Chem. Rev. 2010, 110,5447.  
9 (a) Du, Y.; Lu, X.; Zhang, C., Angew. Chem. Int. Ed. 2003, 42, 1035; (b) Du, Y.; Feng, J.; Lu, X., Org. Lett. 2005, 7, 1987; (c) Feng, J.; Lu, X.; Kong, A.; Han, X., Tetrahedron 2007, 63, 6035; (d) Zheng, S.; Lu, X., Org. Lett. 2008, 10, 4481; (e) Zheng, S.; Lu, X., Tetrahedron Lett.2009, 50, 4532; (f) Zheng, S.; Lu, X., Org. Lett. 2009, 11, 3978; (g) Deng, H.-P.; Wei, Y.; Shi, M., Adv. Synth. Catal. 2012, 354, 783.  
10 (a) Chen, Z. L.; Zhang, J. L., Chem-Asian J. 2010, 5, 1542; (b) Tian, J.; Zhou, R.; Sun, H.; Song, H.; He, Z., J. Org. Chem. 2011, 76, 2374; (c) Xie, P. Z.; Huang, Y.; Chen, R. Y., Org. Lett. 2010, 12, 3768.  
11 (a) Deng, H.-P.; Wei, Y.; Shi, M., Org. Lett. 2011, 13, 3348; (b) Zhong, F.; Han, X.; Wang, Y.; Lu, Y., Angew. Chem. Int. Ed. 2011, 50, 7837; (c) Tan, B.; Candeias, N. R.; Barbas, C. F., J. Am. Chem. Soc. 2011,133, 4672; (d) Ye, L. W.; Sun, X. L.; Wang, Q. G.; Tang, Y., Angew. Chem. Int. Et. 2007, 46, 5951; (e) Wang, Q.-G.; Zhu, S.-F.; Ye, L.-W.; Zhou, C.-Y.; Sun, X.-L.; Tang, Y.; Zhou, Q.-L., Adv. Synth. Catal.2010, 352, 1914; (f) Zhou, R.; Wang, J.; Song, H.; He, Z., Org. Lett.2011, 13, 580.  
12 Zhou, R.; Wang, C.; Song, H.; He, Z., Org. Lett. 2010, 12, 976.  
13 Ye, S.; Wang, T.; Shen, L.-T., Synthesis 2011, 2011, 3359.  
14 (a) Ma, S., Chem. Rev. 2005, 105, 2829; (b) Xu, S.; He, Z. Sci. Sinica Chim. 2010, 40, 856 (in Chinese) (徐四龙; 贺峥杰, 中国科学: 化学2010, 40, 856. ); (c) Zhang, X.-C.; Cao, S.-H.; Wei, Y.; Shi, M., Chem. Commun. 2011, 47, 1548; (d) Zhao, Q.; Han, X.; Wei, Y.; Shi, M.; Lu, Y., Chem. Commun. 2012, 48, 970.  
15 (a) Trost, B. M.; Kazmaier, U., J. Am. Chem. Soc. 1992, 114, 7933; (b) Guo, C.; Lu, X., J. Chem. Soc., Perkin Trans. 1 1993, 1921.
16 (a) Xu, S.; Zhou, L.; Zeng, S.; Ma, R.; Wang, Z.; He, Z., Org. Lett.2009, 11, 3498; (b) Ma, R.; Xu, S.; Tang, X.; Wu, G.; He, Z., Tetrahedron 2011, 67, 1053.  
17 Tang, X.; Zhang, B.; He, Z.; Gao, R.; He, Z., Adv. Synth. Catal. 2007,349, 2007.  
18 Jacobsen, M. J.; Funder, E. D.; Cramer, J. R.; Gothelf, K. V., Org. Lett.2011, 13, 3418.  
19 (a) Tran, Y. S.; Martin, T. J.; Kwon, O., Chem-Asian J. 2011, 6, 2101; (b) Tran, Y. S.; Kwon, O., J. Am. Chem. Soc. 2007, 129, 12632; (c) Guo, H. C.; Xu, Q. H.; Kwon, O., J. Am. Chem. Soc. 2009, 131, 6318; (d) Liang, Y.; Liu, S.; Yu, Z.-X., Synlett 2009, 2009, 905; (e) Martin, T. J.; Vakhshori, V. G.; Tran, Y. S.; Kwon, O., Org. Lett. 2011, 13, 2586; (f) Guan, X.-Y.; Wei, Y.; Shi, M., Eur. J. Org. Chem. 2011, 2011, 2673.
20 Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z., Org. Lett. 2010, 12, 544.  
21 Xu, S.; Zou, W.; Wu, G.; Song, H.; He, Z., Org. Lett. 2010, 12, 3556.  
22 (a) Perez, L. J.; Shimp, H. L.; Micalizio, G. C., J. Org. Chem. 2009, 74,7211; (b) Clark, D. A.; Kulkarni, A. A.; Kalbarczyk, K.; Schertzer, B.; Diver, S. T., J. Am. Chem. Soc. 2006, 128, 15632.  
23 (a) Corey, E. J.; Erickson, B. W., J. Org. Chem. 1974, 39, 821; (b) Date, S. M.; Ghosh, S. K., Angew. Chem. Int. Ed. 2007, 46, 386; (c) He, Z.; Tang, X.; He, Z., Phosphorus Sulfur Silicon Relat. Elem. 2008,183, 1518; (d) Khong, S. N.; Tran, Y. S.; Kwon, O., Tetrahedron 2010,66, 4760; (e) Xu, S.; Chen, R.; He, Z., J. Org. Chem. 2011, 76, 7528.  
24 (a) Liang, Y.; Liu, S.; Xia, Y. Z.; Li, Y. H.; Yu, Z. X., Chem-Eur. J.2008, 14, 4361; (b) Xia, Y.; Liang, Y.; Chen, Y.; Wang, M.; Jiao, L.; Huang, F.; Liu, S.; Li, Y.; Yu, Z.-X., J. Am. Chem. Soc. 2007, 129,3470.  
25 Virieux, D.; Guillouzic, A.-F.; Cristau, H.-J., Tetrahedron 2006, 62,3710.  
26 (a) Berenguer, M. J.; Castells, J.; Galard, R. M.; Moreno-Manas, M., Tetrahedron Lett. 1971, 12, 495; (b) Font, J.; March, P., Tetrahedron Lett. 1978, 19, 3601; (c) Sunggak, K.; Youn, C. K., Tetrahedron Lett.1990, 31, 2901.  
27 Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z., Chem-Eur. J. 2009, 15,8698.
28 Bellur, E.; Feist, H.; Langer, P., Tetrahedron 2007, 63, 10865.  
29 Ma, R. M.S. Thesis, Nankai University, Tianjin, 2010 (in Chinese) (马仁芹, 硕士论文, 南开大学, 天津, 2010)
30 (a) Shi, Y.-L.; Shi, M., Org. Lett. 2005, 7, 3057; (b) Zhao, G.-L.; Shi, Y.-L.; Shi, M., Org. Lett. 2005, 7, 4527; (c) Shi, Y.-L.; Shi, M., Org. Biomol. Chem. 2007, 5, 1499.  
31 Tang, X. M.S. Thesis, Nankai University, Tianjin, 2007 (in Chinese) (汤小芳, 硕士论文, 南开大学, 天津, 2007).
32. Meng, X.; Huang, Y.; Zhao, H.; Xie, P.; Ma, J.; Chen, R., Org. Lett. 2009, 11, 991.  
Options
Outlines

/

〈 〉