Synthetic methodology using tertiary phosphines as nucleophilic catalysts

Pure and Applied Chemistry

Volumn 77, Issue 12, 2005, Pages 1985-1990

  Lu, Xiyan ^a   Du, Yishu ^a   Lu, Cheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allenoates; Dipolarophiles; Nucleophilic catalysts; Synthetic methodology; Tertiary phosphines

Indexed keywords

EID: 29244447356     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200577121985     Document Type: Conference Paper

References (23)

1. For a recent account on phosphine-catalyzed reactions, see: (a) X. Lu, C. Zhang, Z. Xu. Acc. Chem. Res. 34, 535 (2001);
2. for recent reports on phosphine-catalyzed reactions, see: (b) S. A. Frank, D. J. Mergott, W. R. Roush. J. Am. Chem. Soc. 124, 2404 (2002);
3. (c) L.-C. Wang, A. L. Luis, K. Agapiou, H.-Y. Jang, M. J. Krische. J. Am. Chem. Soc. 124, 2402 (2002);
4. (d) C.-K. Jung, J.-C. Wang, M. J. Krische. J. Am. Chem. Soc. 126, 4418 (2004).
5. B. M. Trost and U. Kazmaier. J. Am. Chem. Soc. 114, 7933 (1992);
6. (b) C. Guo and X. Lu. J. Chem. Soc., Chem. Commun. 394 (1993);
7. (c) C. Guo and X. Lu. J. Chem. Soc., Perkin Trans, 1 1921 (1993).
8. B. M. Trost and G. R. Dake. J. Am. Chem. Soc. 119, 7595 (1997).
9. (a) B. M. Trost and C.-J. Li. J. Am. Chem. Soc. 116, 3167 (1994);
10. (b) B. M. Trost and C.-J. Li. J. Am. Chem. Soc. 116, 10819 (1994);
11. (c) C. Zhang and X. Lu. Synlett 645 (1995);
12. (d) B. M. Trost and G. R. Dake. J. Org. Chem. 62, 5670 (1997).
13. C. Zhang and X. Lu. J. Org. Chem. 60, 2906 (1995);
14. (b) Z. Xu and X. Lu. Tetrahedron Lett. 38, 3461 (1997);
15. (c) G. Zhu, Z. Chen, Q. Jiang, D. Xiao, P. Cao, X. Zhang. J. Am. Chem. Soc. 119, 3836 (1997);
16. (d) Z. Xu and X. Lu. J. Org. Chem. 63, 5031 (1998);
17. (e) Z. Xu and X. Lu. Tetrahedron Lett. 40, 549 (1999).
18. Y. Du, X. Lu, Y. Yu. J. Org. Chem. 67, 8901 (2002).
19. Y Du and X. Lu. J. Org. Chem. 68, 6463 (2003).
20. Recently, some spiro heterocycles were constructed by Pyne's group using the phosphine-catalyzed [3+2] cycloaddition reaction. See: (a) S. G. Pyne, K. Schafer, B. W. Skelton, A. H. White. Chem. Commun. 2267 (1997);
21. (b) A. T. Ung, K. Schafer, K. B. Lindsay, S. G. Pyne, K. Amornraksa, R. Wouters, I. Van der Linden, I. Biesmans, I. A. S. J. Lesage, B. W. Skelton, A. H. White. J. Org. Chem. 67, 227 (2002).
22. Y. Du, X. Lu, C. Zhang. Angew. Chem., Int. Ed. 42, 1035 (2003).
23. C. Lu and X. Lu. Org. Lett. 4, 4677 (2002).