Zinc-metal promoted selective α-haloacylation and gem-bisacylation of alkyl aldehydes in the presence of chlorotrimethylsilane

Tetrahedron Letters

Volumn 45, Issue 17, 2004, Pages 3503-3506

  Ishino, Yoshio ^a   Mihara, Masatoshi ^a   Takeuchi, Takeshi ^a   Takemoto, Masanobu ^b  

^a OSAKA MUNICIPAL TECHNICAL RESEARCH INSTITUTE   (Japan)

^b Yamamoto Chemical Ind Co Ltd   (Japan)

Author keywords

Haloalkyl carboxylates; Acylals; TMSCl; Zinc

Indexed keywords

ALDEHYDE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLORINE DERIVATIVE; CHLOROTRIMETHYLSILANE; DICARBOXYLIC ACID; DICHLOROMETHANE; METAL; ZINC;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 1842637247     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.159     Document Type: Article

References (28)

1. For example, Knochel P., Singer R.D. Chem. Rev. 93:1993;2117.
2. Erdik E. Organozinc Reagents in Organic Synthesis. 1996;CRC, Boca Raton, FL.
3. Knochel P., Jones P. Organozinc Reagents: A Practical Approach. 1999;Oxford University Press, New York.
4. Knochel P., Millot N., Rodrigguez A.L., Tucker C.E. Org. React. 58:2001;417.
5. Cardillo G., Simone A.D., Mingardi A., Tomasini C. Synlett. 1995;1131.
6. Yadav J.S., Srinivaa D., Reddy G.S., Bindu K.H. Tetrahedron Lett. 38:1997;8745.
7. Inoue K., Shimizu Y., Shibata I., Baba A. Synlett. 2001;1659.
8. Haslam E. Shikimic Acid Metabolism and Metabolites. 1993;John Wiley and Sons, New York.
9. Ishino Y., Mihara M., Nishihama S., Nishiguchi I. Bull. Chem. Soc. Jpn. 71:1998;2669.
10. Ishino Y., Mihara M., Kageyama M. Tetrahedron Lett. 43:2002;6601.
11. Ito T., Ishino Y., Mizuno T., Ishikawa A., Kobayashi J. Synlett. 2002;2116.
12. Iwai T., Ito T., Mizuno T., Ishino Y. Tetrahedron Lett. 45:2004;1083.
13. Greene T.W.M., Wuts P.M.G. Protective Groups in Organic Synthesis. 3rd ed. 1999;John Wiley and Sons, New York.
14. Michie J.K., Miller J.A. Synthesis. 1981;824.
15. Thomas J.M. Angew. Chem., Int. Ed. Engl. 27:1988;1673.
16. Karimi B., Seradj H., Ebrahimian R.G. Synlett. 2000;623.
17. Carrigan M.D., Eash K.J., Oswald M.C., Mohan R.S. Tetrahedron Lett. 42:2001;8133.
18. Norihiko S., Kuniaki N., Tsuneo S. Synlett. 2001;1921.
19. Curini M., Epifano F., Marcotullio M.C., Rosati O., Nocchetti M. Tetrahedron Lett. 43:2002;2709.
20. Kumar P., Hedge V.R., Kumar T.P. Tetrahedron Lett. 1995;601.
21. Pereira C., Gigante B., Marcelo-Curto M.J., Carreyra H., Perot G., Guisnat M. Synthesis. 1995;1077.
22. Ballini R., Bordoni M., Bosica G., Maggi R., Sartori G. Tetrahedron Lett. 39:1998;7587.
23. Neuenschwnder M., Bigler P., Christen K., Iseli R., Kyburz R. Helv. Chim. Acta. 61:1978;2047.
24. Bigler P., Schonholzer S., Neuenschwnder M. Helv. Chim. Acta. 61:1978;2059.
25. Bigler P., Muhle H., Neuenschwnder M. Synthesis. 1978;593.
26. Chou T.-S., Knochel P. J. Org. Chem. 55:1990;4791.
27. + 298.1205, found 298.1208.
28. Lewis acid catalyzed allylation by indium metal was reported: Lim H.J., Keum G., Kang S.B., Kim Y., Chung B.Y. Tetrahedron Lett. 40:1999;1547.