Synthesis of dienol ethers using the phosphine-catalyzed alkyne isomerization reaction

Synlett

Volumn , Issue 7, 2011, Pages 989-991

  Fu, Michael Yunyi ^a   Guo, Jiawen ^a   Toy, Patrick H ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

alkyne isomerization; dienes; enol ethers; organocatalysis; polymer supported catalyst; triphenylphosphine

Indexed keywords

ALKYNE; DIENOL ETHER; ETHER; PHOSPHINE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ELECTRON; FILTRATION; ISOMERIZATION; NUCLEOPHILICITY; PURIFICATION; SYNTHESIS;

EID: 79954582401     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259700     Document Type: Article

References (38)

1. Guo C, Lu X, J. Chem. Soc., Perkin Trans. 1 1993 1921
2. Lu X, Zhang C, Xu Z, Acc. Chem. Res. 2001 34 535
3. Trost B M., Kazmaier U, J. Am. Chem. Soc. 1992 114 7933
4. For reviews of phosphine catalysis, see:, Methot J L., Roush W R., Adv. Synth. Catal. 2004 346 1035
5. Ye L.-W, Zhou J, Tang Y, Chem. Soc. Rev. 2008 37 1140
6. Marinetti A, Voituriez A, Synlett 2010 174
7. Wei Y, Shi M, Acc. Chem. Res. 2010 43 1005
8. Rychnovsky S D., Kim J, J. Org. Chem. 1994 59 2659
9. Kwong C K.-W, Fu M Y., Lam C S.-L, Toy P H., Synthesis 2008 2307
10. Li M, O'Doherty G A., Org. Lett. 2006 8 3987
11. Li M, O'Doherty G A., Org. Lett. 2006 8 6087
12. Xing Y, O'Doherty G A., Org. Lett. 2009 11 1107
13. Kwong C K.-W, Huang R, Zhang M, Shi M, Toy P H., Chem. Eur. J. 2007 13 2369
14. Kwong C K.-W, Fu M Y., Law H C.-H, Toy P H., Synlett 2010 2617
15. For the use of monofunctional polymer-supported phosphines to catalyze the isomerization of alkynones, see:, Wang Y, Jiang H, Liu H, Liu P, Tetrahedron Lett. 2005 46 3935
16. Liu H.-L, Jiang H.-F, Xu L, Zhan H.-Y, Tetrahedron Lett. 2007 48 8371
17. Kearney A M., Vanderwal C D., Angew. Chem. Int. Ed. 2006 45 7803
18. Steinhardt S E., Silverston J S., Vanderwal C D., J. Am. Chem. Soc. 2008 130 7560
19. Michels T D., Rhee J U., Vanderwal C D., Org. Lett. 2008 10 4787
20. Martin D B. C., Vanderwal C D., J. Am. Chem. Soc. 2009 131 3472
21. Steinhardt S E., Vanderwal C D., J. Am. Chem. Soc. 2009 131 7546
22. Michels T D., Kier M J., Kearney A M., Vanderwal C D., Org. Lett. 2010 12 3093
23. Becher J, Org. Synth. 1979 59 79
24. Becher J, Synthesis 1980 589
25. Soullez D, Plé G, Duhamel L, J. Chem. Soc., Perkin Trans. 1 1997 1639
26. For a related DMAP-catalyzed isomerization reaction that results in the synthesis of -acetoxy dienoates, see:, Yue Y, Yu X.-Q, Pu L, Chem. Eur. J. 2009 15 5104
27. Takimoto M, Shimizu K, Mori M, Org. Lett. 2001 3 3345
28. See Supporting Information for details
29. Capella L, Montevecchi P C., Nanni D, J. Org. Chem. 1994 59 3368
30. Harvey D F., Lund K P., Neil D A., J. Am. Chem. Soc. 1992 114 8424
31. For a review of organic polymer supports, see:, Lu J, Toy P H., Chem. Rev. 2009 109 815
32. For the JandaJel concept, see:, Toy P H., Janda K D., Tetrahedron Lett. 1999 40 6329
33. Toy P H., Reger T S., Janda K D., Aldrichimica Acta 2000 33 87
34. Toy P H., Reger T S., Garibay P, Garno J C., Malikayil J A., Liu G.-Y, Janda K D., J. Comb. Chem. 2001 3 117
35. Choi M K. W., Toy P H., Tetrahedron 2004 60 2903
36. 3, see:, Choi M K. W., He H S., Toy P H., J. Org. Chem. 2003 68 9831
37. Zhao L.-J, He H S., Shi M, Toy P H., J. Comb. Chem. 2004 6 680
38. For a review of polymer-supported phosphines, see:, Guino M, Hii K K., Chem. Soc. Rev. 2007 36 608