An efficient and rapid chalcogenide-Morita-Baylis-Hillman process promoted by TBDMSOTf and a thiolane

Tetrahedron Letters

Volumn 47, Issue 21, 2006, Pages 3553-3556

  Rao, Jamjanam Srivardhana ^a   Brière, Jean François ^a   Metzner, Patrick ^a   Basavaiah, Deevi ^b  

^a UNIVERSITÉ DE CAEN   (France)

^b UNIVERSITY OF HYDERABAD   (India)

Author keywords

Acetal; Chalcogenide Morita Baylis Hillman; Enone; Sulfide; TBDMSOTf

Indexed keywords

ACETAL DERIVATIVE; ALKANE; SULFIDE; THIOL DERIVATIVE;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; LOW TEMPERATURE; MICHAEL ADDITION; TEMPERATURE MEASUREMENT;

EID: 33646074035     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.070     Document Type: Article

References (48)

1. Morita K., Suzuki Z., and Hirose H. Bull. Chem. Soc. Jpn. 41 (1968) 2815
2. Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972.
3. Chem. Abstr. 77 (1972) 34174q
4. For recent reviews, see:. Basavaiah D., Rao P.D., and Hyma R.S. Tetrahedron 52 (1996) 8001
5. Ciganek E. In: Paquette L.A. (Ed). Organic Reactions Vol. 51 (1997), Wiley, New York 201
6. Basavaiah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811
7. Methot J.L., and Roush W.R. Adv. Synth. Catal. 346 (2004) 1035 (phosphine promoters)
8. For reviews on the asymmetric version, see:. Langer P. Angew. Chem., Int. Ed. 39 (2000) 3049
9. Langer P. In: Schmalz H.-G., and Wirth T. (Eds). Organic Synthesis Highlights Vol. 5 (2003), Wiley-VCH, Weinheim 165
10. France S., Guerin D.J., Miller S.J., and Lectka T. Chem. Rev. 103 (2003) 2985 (nucleophilic chiral amines)
11. Berkessel A., and Gröger H. Asymmetric Organocatalysis (2005), Wiley-VCH, Weinheim 182
12. Kataoka T., Iwama T., and Tsujiyama S.-I. Chem. Commun. (1998) 197
13. Kinoshita H., Osamura T., Kinoshita S., Iwamura T., Watanabe S.-I., Kataoka T., Tanabe G., and Muraoka O. J. Org. Chem. 68 (2003) 7532 and references citied therein
14. For a recent exhaustive review covering this field of research, see:. Kataoka T., and Kinoshita H. Eur. J. Org. Chem. (2005) 45
15. For an example of highly effective Chalcogenide-MBH reaction, see:. You J., Xu J., and Verkade J.G. Angew. Chem., Int. Ed. 42 (2003) 5054
16. For selected recent examples making use of Lewis acids, see:. Yamada Y.M.A., and Ikegami S. Tetrahedron Lett. 41 (2000) 2165
17. Aggarwal V.K., Dean D.K., Mereu A., and Willams R. J. Org. Chem. 67 (2002) 510
18. Li G., Xu X., Chen D., Timmons C., Carducci M.D., and Headley A.D. Org. Lett. 5 (2003) 329
19. Yang K.-S., Lee W.-D., Pan J.-F., and Chen K. J. Org. Chem. 68 (2003) 915
20. Matsui K., Takizawa S., and Sasai H. Tetrahedron Lett. 46 (2005) 1943
21. Shiina I., Yamai Y.-S., and Shimazaki T. J. Org. Chem. 70 (2005) 8103
22. For selected recent examples dealing with the reaction rate, see:. Aggarwal V.K., Emme I., and Fulford S.Y. J. Org. Chem. 68 (2003) 692
23. Maher D.J., and Connon S.J. Tetrahedron Lett. 45 (2004) 1301
24. Chandrasekhar S., Narsihmulu C., Saritha B., and Shameem Sultana S. Tetrahedron Lett. 45 (2004) 5865
25. Lin Y.-S., Liu C.-W., and Tsai T.Y.R. Tetrahedron Lett. 46 (2005) 1859
26. Mi X., Luo S., and Cheng J.-P. J. Org. Chem. 70 (2005) 2338
27. Caumul P., and Hailes H.C. Tetrahedron Lett. 46 (2005) 8125
28. Pereira S.I., Adrio J., Silva A.M.S., and Carretero J.-C. J. Org. Chem. 70 (2005) 10175
29. Kataoka T., Iwama T., Tsujiyama S.-I., Kanematsu K., Iwamura T., and Watanabe S.-I. Chem. Lett. (1999) 257
30. Walsh L.M., Winn C.L., and Goodman J.M. Tetrahedron Lett. 43 (2002) 8219
31. For recent reviews, see:. Tietze L.F. Chem. Rev. 96 (1996) 115
32. Pellissier H. Tetrahedron 62 (2006) 1619 and references cited therein
33. For recent discussions about the mechanism, see:. Santos L.S., Pavam C.H., Almeida W.P., Coelho F., and Eberlin M.N. Angew. Chem., Int. Ed. 43 (2004) 4330
34. Aggarwal V.K., Fulford S.Y., and Lloyd-Jones G.C. Angew. Chem., Int. Ed. 44 (2005) 2
35. Price K.E., Broadwater S.J., Walker B.J., and McQuade D.T. J. Org. Chem. 70 (2005) 3980
36. Suzuki M., Kawagishi T., and Noyori R. Tetrahedron Lett. 22 (1981) 1809
37. Kim S., Kim Y.G., and Park J.H. Tetrahedron Lett. 32 (1991) 2043 (pyridine)
38. Hojo M., Nagayoshi M., Fujii A., Yanagi T., Ishibashi N., Miura K., and Hosomi A. Chem. Lett. (1994) 719 (silyl amine)
39. Barrett A.G.M., and Kamimura A.J. J. Chem. Soc., Chem. Commun. (1995) 1755 (an asymmetric version with a silyl sulfide or selenide)
40. Wang F., and Zibuck R. Synlett (1998) 245 (pyridine)
41. Kim S., Park J.H., Kim Y.G., and Lee J.M. J. Chem. Soc., Chem. Commun. (1993) 1188
42. 2Na: 239.1048. Found: 239.1055.
43. It has been shown that the reaction could be promoted by TMSOTf or TESOTf in almost the same efficiency. But, the yields were highly dependent upon the quality of these air sensitive reagents.
44. For an excellent review discussing the reactivity of acetals towards silyl enolethers, see:. Dilman A.D., and Loffe S.L. Chem. Rev. 103 (2003) 733
45. The acetals were either commercially available or prepared following a literature procedure, see:. Leonard N.M., Oswald M.C., Freiberg D.A., Nattier B.C., Smith R.C., and Mohan R.S. J. Org. Chem. 67 (2002) 5202
46. Lee K., Kim H., Miura T., Kiyota K., Kusama H., Kim S., Iwasawa N., and Lee P.H. J. Am. Chem. Soc. 125 (2003) 9682
47. Kim S., Lee S., and Park J.H. Bull. Korean Chem. Soc. 14 (1993) 654
48. 1H NMR at -55 °C, and 68:32 (1:3a) at -40 °C.