Revisiting the Corey-Chaykovsky reaction: The solvent effect and the formation of β-hydroxy methylthioethers

Tetrahedron

Volumn 62, Issue 6, 2006, Pages 1209-1215

  Peng, Yu ^a   Yang, Jin Hui ^a   Li, Wei Dong Z ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

Corey Chaykovsky reaction; Epoxide; Methylthioether; Solvent effect

Indexed keywords

EPOXIDE; ETHER DERIVATIVE; KETONE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL REACTION; COREY CHAYKOVSKY REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 29744462015     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.10.068     Document Type: Article

References (34)

1. For leading references, see: (a) E.J. Corey, and M. Chaykovsky J. Am. Chem. Soc. 84 1962 867 868
2. E.J. Corey, and M. Chaykovsky Tetrahedron Lett. 5 1963 169 171
3. E.J. Corey, and M. Chaykovsky J. Am. Chem. Soc. 86 1964 1640 1641
4. E.J. Corey, and M. Chaykovsky J. Am. Chem. Soc. 87 1965 1353 1364
5. For a general account see: (e) J.S. Ng, and C. Liu L.A. Paquette Encyclopedia of Reagents in Organic Synthesis 1995 Wiley New York 2159 2165
6. For general reviews on S-ylide chemistry, see: (a) B.M. Trost, and L.S. Melvin Sulfur Ylides: Emerging Synthetic Intermediates 1975 Academic New York
7. J. Aubé B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 1 1991 Pergamon Oxford 819 842
8. Some variable conditions have appeared in the literatures, see: (a) E. Akgün, M.B. Glinski, K.L. Dhawan, and T. Durst J. Org. Chem. 46 1981 2730 2734 although LDA/THF system was used, but no sulfide product of type 2 formation were observed therein
9. 3Li/HMPA-THF (v/v 1/4) system was used
10. J.D. White, and T.C. Somers J. Am. Chem. Soc. 116 1994 9912 9920 NaH/HMPA-benzene system was used
11. For phase transfer conditions, see: (d) M.E. Borredon, F. Clavellinas, M. Delmas, A. Gaset, and J.V. Sinisterra J. Org. Chem. 55 1990 501 504
12. P. Mosset, and R. Grée Synth. Commun. 15 1985 749 757
13. For recent reports on the application of this salt, see: (a) L. Alcaraz, K. Coa, A.P. Cridland, E. Kinchin, J. Morris, and S.P. Thompson Org. Lett. 7 2005 1399 1401
14. D.M. Hodgson, M.J. Fleming, and S.J. Stanway Org. Lett. 7 2005 3295 3298
15. To the best of our knowledge, there is only one article in which the abnormal product 2 was recorded as a minor by-product by Roush and co-worker, cf.: W.R. Roush, and S. Rodriguez-Russo J. Org. Chem. 52 1987 603 606 Although Corey and Chaykovsky had described the production of a hydroxy-bearing (according to IR analysis) side-product in their original report (see Section 2 of Ref. 1d), they did not characterize its structure then
16. For relevant pathways leading to the sulfide formation, see: (a) J.B. Bode, and E.M. Carreira J. Org. Chem. 66 2001 6410 6424
17. K. Lee, H. Kim, T. Miura, K. Kiyota, H. Kusama, S. Kim, N. Iwasawa, and P.H. Lee J. Am. Chem. Soc. 125 2003 9682 9688
18. S. Iriuchijima, K. Maniwa, and G. Tsuchihashi J. Am. Chem. Soc. 96 1974 4280 4283
19. B.M. Trost, K. Hiroi, and S. Kurozumi J. Am. Chem. Soc. 97 1975 438 440
20. B.M. Trost, and A.C. Lavoie J. Am. Chem. Soc. 105 1983 5075 5090
21. P. Brownbridge, and S. Warren J. Chem. Soc., Perkin Trans. 1 1977 1131 1141
22. J.R. Shanklin, C.R. Johnson, J. Ollinger, and R.M. Coates J. Am. Chem. Soc. 95 1973 3429 3431
23. R.L. Sowerby, and R.M. Coates J. Am. Chem. Soc. 94 1972 4758 4759
24. M. Yamashita, K. Kitagawa, T. Ohhara, Y. Iida, A. Masumi, I. Kawasaki, and S. Ohta Chem. Lett. 1993 653 656 and references cited therein.
25. D.J. Peterson J. Org. Chem. 32 1967 1717 1720
26. See also: (b) S.P. Tanis, M.C. McMills, and P.M. Herrinton J. Org. Chem. 50 1985 5887 5889
27. T. Fujiwara, Y. Tsuruta, and T. Takeda Tetrahedron Lett. 36 1995 8435 8438
28. A. Padwa, and J.R. Gasdaska Tetrahetron 44 1988 4147 4156
29. For leading references on the formation of this type of product, see: (a) J.J. Harnett, L. Alcaraz, C. Mioskowski, J.P. Martel, T. Le Gall, D.-S. Shin, and J.R. Falck Tetrahedron Lett. 35 1994 2009 2012
30. L. Alcaraz, J.J. Harnett, C. Mioskowski, J.P. Martel, T. Le Gall, D.-S. Shin, and J.R. Falck Tetrahedron Lett. 35 1994 5449 5452
31. For an example of this type of rearrangement, see: W. Kirmse, and B. Kornrumpf Angew. Chem., Int. Ed. 8 1969 75 76
32. W.-D.Z. Li, and Y. Peng Org. Lett. 7 2005 3069 3072
33. In contrast with this remarkable regioslectivity, diol 9 was prepared from triene 7 by Sharpless dihydroxylation with an AD-mix reagent system in a rather low yield (ca. 10%, poor regioselectivity). Similarly, electrophilic epoxidation of triene 7 with m-CPBA also lacks regioselectivity for the production of labile epoxide 5.
34. This is apparently due to the inherent preference for the oxy-3-exo-tet ring closure process. It is evident that the addition of metal (Li, Na, or K) iodide in the reaction mixture (i.e., reaction in Table 1) could not increase the yield of the sulfide formation.