2288
V. Reutrakul et al. / Tetrahedron Letters 43 (2002) 2285–2288
2. (a) Kende, A. S.; Mendoza, J. S. Tetrahedron Lett. 1990,
31, 7105–7108; (b) DePouilly, P.; Che´nede´, A.; Mallet,
J.-M.; Sinay¨, P. Tetrahedron Lett. 1992, 33, 8065–8068; (c)
Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fuku-
moto, K. Synlett 1994, 859–860; (d) Keck, G. E.; Savin, K.
A.; Weglarz, M. A. J. Org. Chem. 1995, 60, 3194–3204; (e)
Marko´, I. E.; Murphy, F.; Kumps, L.; Ates, A.; Touillaux,
R.; Craig, D.; Carballares, S.; Dolan, S. Tetrahedron 2001,
57, 2609–2619 and references cited therein.
and 2897–2902; (i) Mauleo´n, P.; Alonso, I.; Carretero, J.
C. Angew. Chem., Int. Ed. 2001, 40, 1291–1293.
5. For the synthetic utilization of a-halomethyl phenyl sul-
fones, see: (a) Reutrakul, V.; Pohmakotr, M. In Encyclo-
pedia of Reagents for Organic Synthesis; Paquette, L. A.,
Ed.; John Wiley: New York, 1995; Vol. 2, pp. 1165–1168;
(b) Giardina`, A.; Giovannini, R.; Petrini, M. Tetrahedron
Lett. 1997, 38, 1995–1998; (c) Yoshimatsu, M.; Ohara, M.
Tetrahedron Lett. 1997, 38, 5651–5654.
6. The only publication in this area is the recent report on the
use of gem-dibromomethyl aryl sulfones with Sm/SmI2/
CrCl3 (cat.) system for the synthesis of alkylidene sulfones,
see: Liu, Y.; Wu, H.; Zhang, Y. Synth. Commun. 2001, 31,
47–52.
7. All compounds were characterized by spectral data and
elemental analyses or HRMS except those reported in
entry 7, Table 1 (see footnote d).
8. These diastereomers were separated by preparative TLC
on silica gel.
9. For reviews on SmI2, see: (a) Molander, G. A. In Organic
Reactions; Paquette, L. A., Ed.; John Wiley: New York,
1994; Vol. 46, pp. 211–367; (b) Molander, G. A.; Alonse-
Alija, C. Tetrahedron 1997, 53, 8067–8084 and references
cited therein.
3. Taken in part from M.Sc. Theses by Y.C. and S.U.-T.,
Mahidol University, 1996 and 1997, respectively.
4. For selected reviews and references on the chemistry of
a,b-unsaturated sulfones, see: (a) DeLucchi, O.; Pasquato,
L. Tetrahedron 1988, 44, 6755–6794; (b) Simpkins, N. S.
Tetrahedron 1990, 46, 6951–6984; Simpkins, N. S. Sulfones
in Organic Synthesis; Pergamon Press: Oxford, 1993; (c)
Cossu, S.; DeLucchi, O.; Durr, R.; Fabris, F. Synth.
Commun. 1996, 26, 211–216 and references cited therein;
(d) Ba¨ckvall, J.-E.; Chinchilla, R.; Na´jera, C.; Yus, M.
Chem. Rev. 1998, 98, 2291–2312; (e) Na´jera, C.; Yus, M.
Tetrahedron 1999, 55, 10547–10658; (f) Duan, D.-H.;
Huang, X. Synlett 1999, 317–318; (g) Orita, A.; Yoshioka,
N.; Struwe, P.; Braier, A.; Beckmann, A.; Otera, J. Chem.
Eur. J. 1999, 5, 1355–1363; (h) Lee, J. W.; Lee, C.-W.;
Jung, J. H.; Oh, D. Y. Synth. Commun. 2000, 30, 279–283