A novel procedure for the synthesis of multifunctional ketones through the Fukuyama coupling reaction employing dialkylzincs

Tetrahedron Letters

Volumn 45, Issue 39, 2004, Pages 7343-7345

  Mori, Yoshikazu ^a   Seki, Masahiko ^b  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

^b Purchasing Department   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; KETONE DERIVATIVE; THIOESTER; ZINC BROMIDE; ZINC DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; FUKUYAMA COUPLING REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 4444293529     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.148     Document Type: Article

References (21)

1. R.C. Larock Comprehensive Organic Transformations 1999 John Wiley & Sons New York pp 1197-1620
2. R.K. Dieter Tetrahedron 55 1999 4177 and references cited therein
3. H. Tokuyama, S. Yokoshima, T. Yamashita, and T. Fukuyama Tetrahedron Lett. 39 1998 3189
4. T. Shimizu, and M. Seki Tetrahedron Lett. 42 2001 429
5. Y. Mori, and M. Seki Heterocycles 58 2002 125
6. Y. Mori, and M. Seki J. Org. Chem. 68 2003 1571
7. M. Kimura, and M. Seki Tetrahedron Lett. 45 2004 1635
8. 2Zn (Aldrich) was employed for the coupling reaction
9. The Pd/C catalyst employed in this study was purchased from Degussa Japan Co., Ltd and has the following chemical properties: impregnation depth, 200-500 nm (thick shell); reduction degree, 0-25%; Pd dispersion, 35%; water content, less than 3 wt %. The catalyst is commercially available at Degussa Japan Co., Ltd
10. +)
11. T. Miyazaki, Y. Han-ya, H. Tokuyama, and T. Fukuyama Synlett 2004 477
12. E. Nakamura, and I. Kuwajima J. Am. Chem. Soc. 106 1984 3368
13. H. Oshino, E. Nakamura, and I. Kuwajima J. Org. Chem. 50 1985 2804
14. E. Nakamura, and I. Kuwajima Tetrahedron Lett. 27 1986 83
15. E. Nakamura, K. Sekiya, and I. Kuwajima Tetrahedron Lett. 28 1987 337
16. E. Nakamura, S. Aoki, K. Sekiya, H. Oshino, and I. Kuwajima J. Am. Chem. Soc. 109 1987 8056
17. M.J. Rozema, A. Sidduri, and P. Knochel J. Org. Chem. 57 1992 1956
18. F. Langer, A. Devasagayaraj, P.-Y. Chavant, and P. Knochel Synlett 1994 410
19. A. Devasagayaraj, L. Schwink, and P. Knochel J. Org. Chem. 60 1995 3311
20. L. Micouin, and P. Knochel Synlett 1997 327
21. F.F. Kneisel, M. Dochnahl, and P. Knochel Angew. Chem., Int. Ed. 43 2004 1017