The iron(III) chloride-mediated 1,4-addition of mercaptans to α,β-unsaturated ketones and esters under solvent free conditions

Tetrahedron Letters

Volumn 47, Issue 41, 2006, Pages 7375-7380

  Chu, Cheng Ming ^a   Huang, Wan Ju ^a   Lu, Chaowei ^a   Wu, Pohsi ^a   Liu, Ju Tsung ^a   Yao, Ching Fa ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

, Unsaturated ketones; 1,4 Addition; Anhydrous iron(III) chloride; Solvent free

Indexed keywords

ESTER; FERROUS CHLORIDE; KETONE; REAGENT; SOLVENT; THIOL DERIVATIVE;

ARTICLE; ATMOSPHERE; CATALYSIS; CYCLIZATION; MICHAEL ADDITION; REACTION TIME;

EID: 33748310881     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.151     Document Type: Article

References (36)

1. Fluharty A.L. In: Patai S. (Ed). The Chemistry of the Thiol Group (1974), Wiley, New York 589 Part 2
2. Fujita E., and Nagao Y.J. Bioorg. Chem. 6 (1977) 287
3. Julia M., and Badet B. Bull. Soc. Chim. Fr. (1975) 1363
4. Trost B.M., and Keeley D.E. J. Org. Chem. 40 (1975) 2013
5. Shono T., Matsumura Y., Kashimura S., and Hatanaka K. J. Am. Chem. Soc. 101 (1979) 4752
6. Chang Y.-H., and Pinnick H.W. J. Org. Chem. 43 (1978) 373
7. Shono T., Matsumura Y., Kashimura S., and Hatanaka K. J. Am. Chem. Soc. 101 (1979) 4752
8. Bergman E.D., Ginsberg D., and Rappo R. Org. React. 10 (1959) 179
9. Oare D.A., and Heathcock C.A. In: Eliel E.L., and Wilen S.H. (Eds). Topics in Stereochemistry Vol. 9 (1989), Wiley, New York 277
10. Zhu S., and Cohen T. Tetrahedron 53 (1997) 17607
11. Hiemstra H., and Wiberg H. J. Am. Chem. Soc. 103 (1981) 417
12. Suzuki K., Ikekawa A., and Mukaiyama T. Bull. Soc. Chem. Jpn. 55 (1982) 3277
13. Yamashita H., and Mukaiyama T. Chem. Lett. (1985) 363
14. Emori E., Arai T., Sasai H., and Shibasaki M. J. Am. Chem. Soc. 120 (1998) 4043
15. Kobyashi S., Ogawa C., Kawamura M., and Sugiura M. Synlett (2001) 983
16. Bandini M., Cozzi P.G., Giacomini M., Melchiorre P., Selva S., and Umani-Ronchi A. J. Org. Chem. 67 (2002) 3700
17. Srivastava N., and Banik B.K. J. Org. Chem. 68 (2003) 2109
18. Alam M.M., Varala R., and Adapa S.R. Tetrahedron Lett. 44 (2003) 5115
19. Ranu B.C., Dey S.S., and Samanta S. ARKIVOC (2005) 44
20. Garg S.K., Kumar R., and Chakraborti A.K. Tetrahedron Lett. 46 (2005) 1721
21. Garg S.K., Kumar R., and Chakraborti A.K. Synlett (2005) 1370
22. Novak L., Kolontis P., Szantay C., Aszodi D., and Kajtar M. Tetrahedron 38 (1982) 153
23. In our studies, a solution of deionized water was treated with a mixture of 2-cyclohexen-1-one and thiophenol precisely under the conditions given in Tale's paper as follows. Only 15% of the expected product was observed by NMR analysis. As expected, similar results were observed and only 35% and 20% of product, for a 24 h reaction were found when chalcone and trans-4-phenyl-3-butene-2-one were used, respectively:. Khatik G.L., Kumar R., and Chakraborti A.K. Org. Lett. 8 (2006) 2433
24. Shinde P.D., Mahajan V.A., Borate H.B., Tillu V.H., Bal R., Chandwadkar A., and Wakharkar R.D. J. Mol. Catal. A Chem. 216 (2004) 115
25. Sreekumar R., Rugmini P., and Padmakumar R. Tetrahedron Lett. 38 (1997) 6557
26. Sheldon R.A. Chirotechnology: Industrial Synthesis of Optically Active Compounds (1993), Dekker, New York
27. Laszlo P., Montaufier M.-T., and Randriamahefa S.L. Tetrahedron Lett. 31 (1990) 4867
28. Christoffers J. Synlett (2001) 763
29. Nakamura M., Matsuo K., Ito S., and Nakamura E. J. Am. Chem. Soc. 126 (2004) 3686
30. Nakamura M., Hirai A., and Nakamura E. J. Am. Chem. Soc. 122 (2000) 978
31. Nakamura M., Matsuo K., Inoue T., and Nakamura E. Org. Lett. 5 (2003) 1373
32. Martin R., and Fürstner A. Angew. Chem., Int. Ed. 43 (2004) 3955
33. Nagano T., and Hayashi T. Org. Lett. 6 (2004) 1297
34. Bedford R.B., Bruce D.W., Frost R.M., Goodby J.W., and Hird M. Chem. Commun. (2004) 2822
35. Bodwell J.R., Patwardhan B.H., and Dittmer D.C. J. Org. Chem. 49 (1984) 4192
36. Firouzabadi H., Iranpoor N., and Jafari A.A. Synlett (2005) 299