1272
E. TORRENTE ET AL.
Typical Procedure: [1R,2R,S(S)]-N-{1-(4-bromophenyl)-2-
(phenylselanyl)-2-[2-(S)-(p-tolylsulfinyl)phenyl]ethyl}p-toluenesulfinamide
A solution of n-BuLi (2.3 M in hexane, 0.54 mmol) was added over iPr2NH
(0.74 mmol, 1.8 equiv) in THF (2 mL) at 0◦C. After 10 min stirring, the mixture was
cooled to −98◦C, and the solution of the nucleophile (0.38 mmol, 1 equiv) in THF
(2 mL) was added. After 5 min stirring, N-sulfinylimine (0.76 mmol) was added at
−98◦C in THF (1 mL). When the reaction was completed (5–10 min), the mixture was
hydrolyzed with saturated aqueous NH4Cl (3 mL) and extracted with CH2Cl2 (3 × 10 mL).
The combined organic layers were dried over Na2SO4, and the solvent was removed
under reduced pressure. The residue was purified by flash column chromatography
(hexane/EtOAc 1:1). [1R,2R,S(S)]-N-{1-(4-bromophenyl)-2-(phenylselanyl)-2-[2-(S)-
(p-tolylsulfinyl)phenyl)ethyl}p-toluene-sulfinamide (anti-5c). Yield: 70%; 1H NMR
(200 MHz, CDCl3): δ 7.87 (d, 1H, J = 7.2 Hz), 7.64–6.83 (m, 15H), 6.76 (d, 3H, J =
8.6 Hz) 6.57 (d, 2H, J = 6.8 Hz), 4.90 (d, 1H, J = 10.6 Hz), 4.75 (dd, 1H, J = 10.6 and 7.4
Hz), 5.03 (d, 1H, J = 7.4 Hz), 2.31 (s, 3H), 2.29 (s, 3H) ppm; 13C NMR (50 MHz, CDCl3):
δ 141.84, 140.69, 139.85, 135.09, 132.24, 130.81, 130.42, 130.10, 129.26, 128.70, 128.32,
127.85, 127.67, 127.33, 125.97, 125.44, 121.36, 61.76, 47.24, 21.49, 21.31 ppm.
REFERENCES
1. (a) Mugesh, G.; du Mont, W. W.; Sies, H. Chem. Rev. 2001, 101, 2125–2179; (b) Nogueria, C.
W.; Zeni, G.; Roch, J. B. T. Chem. Rev. 2004, 104, 6255–6285.
2. Sehnem, J. A.; Vargas, F.; Milani, P.; Nascimento, V.; Braga, A. L. Synthesis 2008, 1262–1268.
3. For a comprehensive review about the use of chiral organoselenium in asymmetric catalysis
see: (a) Wirth, T. Tetrahedron 1999, 55, 1–28; (b) Wirth, T. Angew. Chem., Int. Ed. 2000, 39,
3741–3744; (c) Braga, A. L.; Lu¨dtke, D. S.; Vargas, F.; Braga, R. C. Synlett 2006, 1453–1466;
(d) Braga, A. L.; Lu¨dtke, D. S.; Vargas, F. Curr. Org. Chem. 2006, 10, 1921–1938.
4. (a) Braga, A. L.; Lu¨dtke, D. S.; Paixao, M. W.; Alberto, E. E.; Stefani, H. A.; Juliano L. Eur. J.
Org. Chem. 2005, 4260–4264; (b) Tiecco, M.; Testaferri, L.; Bagnoli, L.; Scarponi, C.; Temperini,
A.; Marini, F.; Santi, C. Tetrahedron: Asymmetry 2007, 18, 2758–2767.
5. (a) Braga, A. L.; Scheneider, P. H.; Paixao, M. W.; Deobald, A. M.; Peppe, C.; Bottega, D. P.
J. Org. Chem. 2006, 71, 4305–4307; (b) Sureshkumar, D.; Gunasundari, T.; Saravan, V.; Chan-
drasekaran, S. Tetrahedron Lett. 2007, 48, 623–626; (c) Braga, A. L.; Schwab, R. S.; Alberto, E.
E.; Salman, S. M.; Vargas, J.; Arezedo, J. B. Tetrahedron Lett. 2009, 50, 2309–2311; (d) Ganesh,
V.; Chandrasekaran, S. Synthesis 2009, 3267–3278.
6. Tiecco, M.; Carlone, A.; Sternativo, S.; Marina, F.; Bartoli, G.; Melchiorre, P. Angew. Chem. Int.
Ed. 2007, 46, 6882–6885.
7. Capperucci, A.; Tiberi, C.; Pollicino, S.; Degl‘Innocenti A. Tetrahedron Lett. 2009, 50,
2808–2810 and reference cited therein.
8. (a) Garc´ıa Ruano, J. L.; Carren˜o, M. C.; Toledo, M. A.; Aguirre, J. M.; Aranda, M. T.; Fisher, J.
Angew. Chem. Int. Ed. 2000, 39, 2736–2737; (b) Garc´ıa Ruano, J. L.; Aranda, M. T.; Aguirre, J.
M. Tetrahedron, 2004, 60, 5383–5392; (c) Garc´ıa Ruano, J. L.; Alema´n, J.; Soriano, J. F. Org.
Lett. 2003, 5, 677–680; (d) Garc´ıa Ruano, J. L.; Alema´n, J.; Cid, B. Synthesis 2006, 687–691;
(e) Garc´ıa Ruano, J. L.; Alema´n, Parra, A. J. Am. Chem. Soc. 2005, 127, 13048–13054; (f) Garc´ıa
Ruano, J. L.; Alema´n, J.; Alonso, I.; Parra, A.; Marcos, V.; Aguirre, J. Chem. Eur. J. 2007, 13,
6179–6195; (g) Garc´ıa Ruano, J. L.; Schoepping, C.; Alvarado, C.; Alema´n, J. Chem. Eur. J.
2010, 16, 8968–8971.
9. (a) Garc´ıa Ruano, J. L.; Alema´n, J. Org. Lett. 2003, 5, 4513–4516; (b) Arroyo, Y.; Meana, A.;
Rodr´ıguez, J. F.; Santos, M.; Sanz-Tejedor M. A.; Garc´ıa Ruano, J. L. J. Org. Chem. 2005,