B. Macia´ et al. / Tetrahedron Letters 46 (2005) 6101–6104
6103
for instance: (b) Alonso, E.; Guijarro, D.; Yus, M.
Tetrahedron 1995, 51, 2699–2708.
9. For reviews, see: (a) Yus, M. Chem. Soc. Rev. 1996, 25,
In conclusion, we have described herein the simplest way
to perform the [2,3]-Wittig rearrangement from non-
activated substrates by an arene-catalysed chlorine–lith-
ium exchange starting from easily available allylic chloro-
methyl ethers.25 This new and versatile methodology can
be applied to the total synthesis of interesting naturally
occurring complex molecules.4
´
155–161; (b) Ramon, D. J.; Yus, M. Eur. J. Org. Chem.
2000, 225–237; (c) Yus, M. Synlett 2001, 1197–1205; (d)
´
Yus, M.; Ramon, D. J. J. Latv. Chem. 2002, 79–92; (e)
´
Ramon, D. J.; Yus, M. Rev. Cubana Quim. 2002, 14, 75–
115; (f) Yus, M. In The Chemistry of Organolithium
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Acknowledgements
10. For mechanistic studies, see: (a) Yus, M.; Herrera, R. P.;
Guijarro, A. Tetrahedron Lett. 2001, 42, 3455–3458; (b)
Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2002,
8, 2574–2708.
´
This work was generously supported by the Direccion
General de Ensenanza Superior (DGES) of the current
˜
11. For a polymer supported arene-catalysed version of this
´
Spanish Ministerio de Educacion y Ciencia (MEC;
´
reaction, see: (a) Gomez, C.; Ruiz, S.; Yus, M. Tetra-
Grant No. CTQ2004-01261) and the Generalitat Valen-
ciana (Grant No. GRUPOS03/135). B.M. thanks the
MEC for a predoctoral fellowship. We also thank
MEDALCHEMY S.L. for a gift of chemicals.
´
hedron Lett. 1998, 39, 1397–1400; (b) Gomez, C.; Ruiz, S.;
Yus, M. Tetrahedron 1999, 55, 7017–7026; (c) Yus, M.;
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Gomez, C.; Candela, P. Tetrahedron 2002, 58, 6207–6210;
(d) Arnauld, T.; Barrett, A. G. M.; Hopkins, B. T.
Tetrahedron Lett. 2002, 43, 1081–1083.
12. For a review, see: Guijarro, D.; Yus, M. Recent Res. Dev.
Org. Chem. 1998, 2, 713–744.
Supplementary data
´
13. For reviews, see: (a) Najera, C.; Yus, M. Trends Org.
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Chem. 1991, 2, 155–181; (b) Najera, C.; Yus, M. Org.
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Prep. Proc. Int. 1995, 27, 383–457; (c) Najera, C.; Yus, M.
Recent Res. Dev. Org. Chem. 1997, 1, 67–96; (d) Yus, M.;
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