`
S. Miniere et al. / Tetrahedron: Asymmetry 15 (2004)3275–3280
3280
13. Aggarwal, V. K.; Ford, J. G.; Fonquerna, S.; Adams, H.;
Jones, R. V. H.; Fieldhouse, R. J. Am. Chem. Soc. 1998,
120, 8328–8339.
recently emerged for stereocontrolled dialkylzinc addi-
tion to aldehydes,7,37,38 allylic alkylations,31,39–42 and
Diels–Alder cycloadditions.43 We have shown herein
that the sulfur ylide epoxidation can be made asymmet-
ric with a catalytic amount of ferrocenyl sulfides, and
the first applications of planar chirality to this reaction.
´
14. Solladie-Cavallo, A.; Diep-Vohuule, A.; Sunjic, V.; Vinko-
vic, V. Tetrahedron: Asymmetry 1996, 7, 1783–1788.
´
15. Solladie-Cavallo, A.; Roje, M.; Isarno, T.; Sunjic, V.;
Vinkovic, V. Eur. J. Org. Chem. 2000, 1077–1080.
16. Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y. Z.; Li, F.-W.
J. Org. Chem. 1996, 61, 489–493.
4. Experimental
17. Julienne, K.; Metzner, P.; Henryon, V.; Greiner, A. J.
Org. Chem. 1998, 63, 4532–4534.
18. Julienne, K.; Metzner, P.; Henryon, V. J. Chem. Soc.,
Perkin Trans. 1 1999, 731–736.
4.1. Typical epoxidation procedure
19. Hayakawa, R.; Shimizu, M. Synlett 1999, 1328–
1330.
20. Saito, T.; Akiba, D.; Sakairi, M.; Kanazawa, S. Tetrahe-
dron Lett. 2001, 42, 57–59.
21. Saito, T.; Akiba, D.; Sakairi, M.; Ishikawa, K.; Otani, T.
Arkivoc 2004(ii), 152–171.
22. Miyake, Y.; Oyamada, A.; Nishibayashi, Y.; Uemura, S.
Heteroatom Chem. 2002, 13, 270–275.
23. Ishizaki, M.; Hoshino, O. Heterocycles 2002, 57, 1399–
1402.
24. Aggarwal, V. K.; Alonso, E.; Hynd, G.; Lydon, K. M.;
Palmer, M. J.; Porcelloni, M.; Studley, J. R. Angew.
Chem., Int. Ed. 2001, 40, 1430–1433.
To a solution of sulfide (17mg, 0.05mmol) in t-BuOH/
H2O 9:1 (415lL) was added benzyl bromide (60lL,
0.50mmol), aldehyde (0.25mmol), NaI (38mg,
0.25mmol), and NaOH (20mg, 0.50mmol). The reac-
tion mixture was stirred at room temperature and mon-
itored by TLC using n-heptane/ethyl acetate (v/v: 9:1).
Water (1mL) was then added and the aqueous phase
was extracted with dichloromethane (3 · 2mL). The
combined organic phases were dried over MgSO4 and
concentrated to dryness. Column chromatography using
n-heptane/ethyl acetate afforded the desired oxirane.25,27
25. Zanardi, J.; Leriverend, C.; Aubert, D.; Julienne, K.;
Metzner, P. J. Org. Chem. 2001, 66, 5620–5623.
26. Winn, C. L.; Bellenie, B. R.; Goodman, J. M. Tetrahedron
Lett. 2002, 43, 5427–5430.
27. Aggarwal, V. K.; Alonso, E.; Bae, I.; Hynd, G.; Lydon, K.
M.; Palmer, M. J.; Patel, M.; Porcelloni, M.; Richardson,
J.; Stenson, R. A.; Studley, J. R.; Vasse, J.-L.; Winn, C. L.
J. Am. Chem. Soc. 2003, 125, 10926–10940.
Acknowledgements
We gratefully acknowledge the ÔPunchOrgaÕ Network
ˆ
(Pole Universitaire Normand de Chimie Organique),
`
the ÔMinistere de la Recherche et des Nouvelles Technol-
ogiesÕ, CNRS (Centre National de la Recherche Scien-
`
´
28. Miniere, S.; Reboul, V.; Arrayas, R. G.; Metzner, P.;
Carretero, J. C. Synthesis 2003, 2249–2254.
29. Watts, W. E. J. Organomet. Chem. Libr. 1979, 7, 399–
459.
´
tifique), the ÔRegion Basse-NormandieÕ and the
European Union (FEDER funding) for financial sup-
`
port. We also thank warmly Dr. Jean-Franc¸ois Briere
(Caen), Prof. Serge Piettre and Dr. Isabelle Chataigner
(Rouen) for fruitful discussions and collaboration.
30. Tarraga, A.; Molina, P.; Luis Lopez, J.; Espinosa, A.;
Evans, D. J. Tetrahedron Lett. 2002, 43, 4717–4720.
31. Bernardi, L.; Bonini, B. F.; Comes-Franchini, M.; Fochi,
M.; Mazzanti, G.; Ricci, A.; Varchi, G. Eur. J. Org. Chem.
2002, 2776–2784.
References
32. Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am.
Chem. Soc. 2002, 124, 5747–5756.
33. Ermolaeva, L. I.; Mastryukov, V. S.; Allinger, N. L.;
Almenningen, A. J. Mol. Struct. 1989, 196, 151–156.
34. Aggarwal, V. K.; Calamai, S.; Ford, G. J. J. Chem. Soc.,
Perkin Trans. 1 1997, 593–599.
1. Tye, H.; Comina, P. J. J. Chem. Soc., Perkin Trans. 1
2001, 1729–1747.
2. Blaser, H. U.; Schmidt, E. Asymmetric Catalysis on
Industrial Scale: Challenges, Approaches and Solutions;
Wiley-VCH: Weinheim, 2004.
3. Breuer, M.; Ditrich, K.; Habicher, T.; Hauer, B.; Kesseler,
M.; Sturmer, R.; Zelinski, T. Angew. Chem., Int. Ed. 2004,
35. Aggarwal, V. K.; Richardson, J. Chem. Commun. 2003,
2644–2651.
¨
43, 788–824.
´
´
´
36. Masdeu-Bulto, A. M.; Diegueza, M.; Martin, E.; Gomez,
M. Coord. Chem. Rev. 2003, 242, 159–201.
37. Priego, J.; Mancheno, O. G.; Cabrera, S.; Carretero, J. C.
Chem. Commun. 2001, 2026–2027.
4. Togni, A.; Hayashi, T. Ferrocenes; VCH: Weinheim, 1995.
5. Togni, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1475–
1477.
6. Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry
1998, 9, 2377–2407.
38. Priego, J.; Manchen˜o, O. G.; Cabrera, S.; Carretero, J. C.
J. Org. Chem. 2002, 67, 1346–1353.
7. Colacot, T. J. Chem. Rev. 2003, 3101–3118.
8. Dai, L. X.; Tu, T.; You, S. L.; Deng, W. P.; Hou, X. L.
Acc. Chem. Res. 2003, 36, 659–667.
9. Atkinson, R. C. J.; Gibson, V. C.; Long, N. J. Chem. Soc.
Rev. 2004, 33, 313–328.
39. You, S.-L.; Zhou, Y.-G.; Hou, X.-L.; Dai, L. X. Chem.
Commun. 1998, 2765–2766.
40. Enders, D.; Peters, R.; Lochtman, R.; Raabe, G.; Run-
sink, J.; Bats, J. W. Eur. J. Org. Chem. 1999, 3399–
3426.
´
10. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997,
97, 2341–2372.
11. Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37,
611–620.
12. Aggarwal, V. K.; Ford, J. G.; Thompson, A.; Jones, R. V.
H.; Standen, M. C. H. J. Am. Chem. Soc. 1996, 118, 7004–
7005.
41. Priego, J.; Manchen˜o, O. G.; Cabrera, S.; Arrayas, R. G.;
Llamas, T.; Carretero, J. C. Chem. Commun. 2002, 2512–
2513.
42. You, S.-L.; Hou, X.-L.; Dai, L.-X.; Yu, Y.-H.; Xia, W. J.
Org. Chem. 2002, 67, 4684–4695.
43. Manchen˜o, O. G.; Arrayas, R. G.; Carretero, J. C. J. Am.
Chem. Soc. 2004, 126, 456–457.
´