Unprecedented carbocyclization of 1,6-allenynes on addition of organoboronic acids under Pd-catalysis

Tetrahedron Letters

Volumn 46, Issue 13, 2005, Pages 2247-2250

  Gupta, Arun Kumar ^a   Rhim, Chul Yun ^a   Oh, Chang Ho ^a  

^a Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; BORONIC ACID DERIVATIVE; PALLADIUM; PHOSPHINE;

ADDITION REACTION; ARTICLE; CATALYSIS; CYCLIZATION; ELECTRON TRANSPORT; MOLECULE; PAUSON KHAND REACTION; REACTION ANALYSIS;

EID: 14744305211     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.020     Document Type: Article

References (29)

1. Brummond, K. M.; Chen, H. Abstracts of Papers, 224th ACS National Meeting, Boston, MA, United States, August 2002; 18
2. K.M. Brummond, and D. Gao Org. Lett. 5 2003 3491
3. B. Alcaido, P. Almendros, and C. Aragoncillo Org. Lett. 5 2003 3795
4. R. Zimmer, C.U. Dinesh, E. Nanadanan, and F.A. Khan Chem. Rev. 100 2000 3067
5. B.M. Trost, F.D. Toste, and A.B. Pinkerton Chem. Rev. 101 2001 2067
6. H. Cao, J. Flippen-Anderson, and J.M. Cook J. Am. Chem. Soc. 125 2003 3230
7. K.M. Brummond, A.D. Kerekes, and H. Wan J. Org. Chem. 67 2002 5156
8. B.L. Pagenkopf, D.B. Belanger, D.J.R. O'Mahony, and T. Livinghouse Synthesis 2000 1009
9. C. Mukai, I. Nomura, and S. Kitagaki J. Org. Chem. 68 2003 1376
10. T. Shibata, S. Kadowaki, M. Hirase, and K. Takagi Synlett 2003 57
11. T. Shibata, S. Kadowaki, and K. Takagi Organometallics 23 2004 4116
12. C. Aubert, O. Buisine, and M. Malacria Chem. Rev. 102 2002 813
13. D. Llerena, C. Aubert, and M. Malacria Tetrahedron Lett. 37 1996 7027
14. K.M. Brummond, H. Chen, P. Sill, and L. You J. Am. Chem. Soc. 124 2002 15186
15. S. Shin, and T.V. Rajan Babu J. Am. Chem. Soc. 123 2001 8416
16. T. Shibata, Y. Takesue, S. Kadowaki, and K. Takagi Synlett 2003 268
17. C.H. Oh, S.H. Jung, and C.Y. Rhim Tetrahedron Lett. 42 2001 8669
18. C.H. Oh, S.H. Jung, D.I. Park, and J.H. Choi Tetrahedron Lett. 45 2004 2499
19. C.H. Oh, H.H. Jung, and K.S. Kim Angew. Chem., Int. Ed. 42 2003 805
20. C.H. Oh, T.W. Ahn, and V.R. Reddy Chem. Commun. 2003 2622
21. C.H. Oh, S.H. Jung, S.Y. Bang, and D.I. Park Org. Lett. 4 2002 3325
22. N. Kim, K.S. Kim, A.K. Gupta, and C.H. Oh Chem. Commun. 2004 618
23. C.H. Oh, S.J. Park, J.H. Ryu, and A.K. Gupta Tetrahedron Lett. 45 2004 7039
24. J.H. Ryu, and C.H. Oh Bull. Chem. Soc. Korea 24 2003 1563
25. U. Hirokazu, and F. Sato Tetrahedron Lett. 39 1998 7329
26. Ma. Shengming, and S. Zhao J. Am. Chem. Soc. 121 1999 7943
27. K. Mikami, and A. Yoshida Tetrahedron 57 2001 889
28. 4 and the solvent was evaporated under vacuum. The crude syrup thus obtained was purified by column chromatography by elution with 1:4 ethyl acetate:hexane to obtain pure products 5aa-da
29. M. Majewski, M.N. Irvine, and J. MacKinnon Tetrahedron: Asymmetry 6 1995 1837