Regioselective Pd-catalyzed alkylative lactonizations of 4-hydroxy-2-alkynecarboxylates with organoboronic acids

Tetrahedron Letters

Volumn 45, Issue 38, 2004, Pages 7039-7042

  Oh, Chang Ho ^a   Park, Su Jin ^a   Ryu, Jin Hyang ^a   Gupta, Arun Kumar ^a  

^a Hanyang University   (South Korea)

Author keywords

Boronic acid; Butenolides; Catalyst; Lactonization; Palladium

Indexed keywords

BUTENOLIDE; CARBOXYLIC ACID DERIVATIVE; ORGANOBORON DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; LACTONIZATION; METHODOLOGY; STEREOCHEMISTRY;

EID: 4444366265     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.129     Document Type: Article

References (36)

1. S. Ma, and Z. Shi J. Org. Chem. 63 1998 6387
2. R. Kazauskas, P.T. Murphy, R.J. Quinn, and R.J. Wells Tetrahedron Lett. 18 1977 37
3. J.A. Pettus Jr., R.M. Wing, and J.J. Sims Tetrahedron Lett. 18 1977 41
4. K.R.H. Repke, R. Megges, J. Weiland, and R. Schon Angew. Chem., Int. Ed. Engl. 34 1995 282
5. S. Zapf, T. Anke, and O. Sterner Acta Chem. Scand. 49 1995 233
6. L.I. Scott, and H.M. Lamb Drugs 3 1999 499
7. Y.-W. Guo, M. Gavagnin, E. Mollo, E. Trivellone, and G. Cimino J. Nat. Prod. 62 1999 1194
8. V.J.R.V. Mukku, M. Speitling, H. Laatsch, and E. Helmke J. Nat. Prod. 63 2000 1570
9. E. Yoneda, T. Kaneko, S.-W. Zhang, K. Onitsuka, and S. Takahashi Org. Lett. 2 2000 441
10. S. Ma, Z. Shi, and Z. Yu Tetrahedron Lett. 40 1999 2393
11. T.R. Hoye, S.M. Donaldson, and T.J. Vos Org. Lett. 1 1999 277
12. B.M. Trost, F.D. Toste, and K. Greenman J. Am. Chem. Soc. 125 2003 4518
13. B.M. Trost, I. Hachiya, and M.C. McIntosh Tetrahedron Lett. 39 1998 6445
14. G. Liu, and X. Lu Tetrahedron Lett. 43 2002 6791
15. A.A. Pletnev, Q. Tian, and R.C. Larock J. Org. Chem. 67 2002 9276
16. R.C. Larock, and Q. Tian J. Org. Chem. 66 2001 7372
17. J. Oyamada, W. Lu, C. Jia, T. Kitamura, and Y. Fujiwara Chem. Lett. 2002 20
18. C. Jia, W. Lu, J. Oyamada, T. Kitamura, K. Matsuda, M. Irie, and Y. Fujiwara J. Am. Chem. Soc. 122 2000 7252
19. A. Arcadi, E. Bernocchi, A. Burini, S. Cacchi, F. Marinelli, and B. Pietroni Tetrahedron 44 1988 481
20. S. Ma, N. Jiao, S. Zhao, and H. Hou J. Org. Chem. 67 2002 2837
21. S. Ma, and Z. Shi Chem. Commun. 2002 540
22. S. Ma, and L. Li Org. Lett. 2 2000 941
23. S. Ma, D. Duan, and Z. Shi Org. Lett. 2 2000 1419
24. S. Ma, and S. Zhao Org. Lett. 2 2000 2495
25. U. Anwar, R. Grigg, and V. Sridharan Chem. Commun. 2000 933
26. R. Grigg, W. MacLachlan, and M. Rasparini Chem. Commun. 2000 2241
27. J. Franzán, and J.-E. Bäckvall J. Am. Chem. Soc. 125 2003 6056
28. M. Rubin, J. Markov, S. Chuprakov, D.J. Wink, and V. Gevorgyan J. Org. Chem. 68 2003 6251
29. C.H. Oh, H.H. Jung, and K.S. Kim Angew. Chem., Int. Engl. 42 2003 805
30. C.H. Oh, H.H. Jung, H.R. Sung, and J.D. Kim Tetrahedron 57 2001 1723
31. C.H. Oh, T.W. Ahn, and V.R. Reddy Chem. Commun. 22 2003 2622
32. C.H. Oh, S.H. Jung, S.Y. Bang, and D.I. Park Org. Lett. 4 2002 3325
33. C.H. Oh, K.S. Kim, and A.K. Gupta Chem. Commun. 22 2004 618
34. K. Itami, T. Kamei, and J.-I. Yoshida J. Am. Chem. Soc. 125 2003 14670
35. C.H. Oh, and H.R. Sung Bull. Korean Chem. Soc. 24 2003 1563
36. K. Mikami, and A. Yoshida Tetrahedron 57 2001 889