Zinc mediated propenylation of Baylis-Hillman acetates

Tetrahedron Letters

Volumn 48, Issue 34, 2007, Pages 5999-6001

  Srihari, P ^a   Singh, Ashutosh Pratap ^a   Basak, A K ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,5 Diene; Allyl bromide; Allyl trimethylsilane; Baylis Hillman acetates; Metathesis

Indexed keywords

ACETIC ACID DERIVATIVE; ZINC;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 34447645477     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.120     Document Type: Article

References (35)

1. Hoffmann H.M.R., and Rabe J. Angew. Chem., Int. Ed. Engl. 24 (1985) 94
2. Basavaiah D., Bakthadoss M., and Pandiarau S. Chem. Commun. (1998) 1639
3. Baylis, A. B.; Hillman, M. E. D. German Patent 2,155,113, 1972; Chem. Abstr. 1972, 77, 34174q.
4. Basavaiah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811 and references cited therein
5. Buchholz R., and Hoffmann H.M.R. Helv. Chim. Acta 74 (1991) 1213
6. Lee K.Y., Kim J.M., and Kim J.N. Tetrahedron Lett. 44 (2003) 6737
7. Wan Q., Cho Y.S., Lambert T.H., and Danishefsky S.J. J. Carbohydr. Chem. 24 (2005) 425
8. Kang S.W., Heo E.Y., Jun J.G., and Kim S.H. Bull. Korean Chem. Soc. 25 (2004) 1924
9. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4490
10. Bao W., Zheng Y., and Zhang Y. J. Chem. Res. (S) (1999) 732
11. Hao N.C., Mavrov M.V., Chrelashvili Z.G., and Serebryakov E.P. Izv. Akad. Nauk SSSR (1988) 1042
12. Dreyfuss M.P. J. Org. Chem. 22 (1975) 423
13. Petrier C., Einhorn J., and Luche J.L. Tetrahedron Lett. 26 (1985) 1449
14. Fukuma T., Lock S., Miyoshi N., and Wada M. Chem. Lett. 31 (2002) 376
15. Torii S., Tanaka H., Yamashita S., and Ikemato Y. Tetrahedron Lett. 14 (1988) 1721
16. Bandini M., Cozzi P.G., Umani-Ronchi A., and Villa M. Tetrahedron 55 (1999) 8103
17. Wilson S.R., and Guazzaroni M.E. J. Org. Chem. 54 (1989) 3087
18. Kjonaas R.A., and Vawter E.J. J. Org. Chem. 51 (1986) 3993
19. Fleming I., Dunogues J., and Smithers R. Org. React. 37 (1989) 57
20. Hunter R., and Tomlinson G.D. Tetrahedron Lett. 30 (1989) 2013
21. Hosomi A., Endo M., and Sakurai H. Chem. Lett. (1976) 941
22. McCluskey A., Mayer D.M., and Young D.J. Tetrahedron Lett. 38 (1997) 5217
23. Tanaka H., Yamashita S., Ikemoto Y., and Torii S. Tetrahedron Lett. 29 (1988) 1721
24. Komatsu N., Uda M., Suzuki H., Takahashi T., Domae T., and Wada M. Tetrahedron Lett. 38 (1997) 7215
25. Konig K., and Neumann W.P. Tetrahedron Lett. (1967) 495
26. Keck G.E., and Yu T. Org. Lett. I (1999) 289
27. Basavaiah D., Sarma P.K.S., and Bhavani A.K.D. J. Chem. Soc., Chem. Commun. (1994) 1091
28. Das B., Banerjee J., Mahender G., and Majhi A. Org. Lett. 6 (2004) 3349
29. Navarre L., Darses S., and Genet J.-P. Chem. Commun. (2004) 1108
30. Yadav J.S., Reddy B.V.S., Basak A.K., Narsaiah A.V., Prabhakar A., and Jagadeesh B. Tetrahedron Lett. 46 (2005) 639
31. Srihari P., Singh A.P., Jain R., and Yadav J.S. Synthesis (2006) 2772
32. Yadav J.S., Gupta M.K., Pandey S.K., Reddy B.V.S., and Sarma A.V.S. Tetrahedron Lett. 46 (2005) 2761
33. Yadav J.S., Reddy B.V.S., and Madan C. New. J. Chem. 25 (2001) 1114
34. No attempts were made to characterize the byproducts formed when the nitrile-containing compounds were used.
35. 3) δ 0.88 (t, 3H, J = 6.5 Hz), 1.07 (t, 3H, J = 6.8 Hz), 2.02-2.08 (m, 2H), 2.13-2.23 (m, 2H), ...