Yinuo Wu et al.
COMMUNICATIONS
Experimental Section
[7] C. Bolm, F. Bienewald, Angew. Chem. 1995, 107, 2883–
2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640–
2642.
[8] a) J. Skarzewski, E. Ostrycharz, R. Siedlecka Tetrahe-
dron: Asymmetry 1999, 10, 3457–3461; b) C. Ohta, H.
Shimizu, A. Kondo, T. Katsuki Synlett 2002, 1, 161–
163; c) K. P. Bryliakov, N. N. Karpyshev, S. A. Fomin-
sky, A. G. Tolstikov, E. P. Talsi, J. Mol. Catal. A: Chem.
2001, 171, 73–80.
[9] J. Skarzewski, E. Ostrycharz, R. Siedlecka, M. Zielin-
ska-Blajet, B. Pisarski, J. Chem. Res. 2001, 263–264.
[10] N. N. Karpyshev, O. D. Yakovleva, E. P. Talsi, K. P. Bry-
liakov, O. V. Tolstikova, J. Mol. Catal. A: Chem. 2000,
157, 91–95.
[11] a) X. Jia, X. Li, L. Xu, Y. Li, Q. Shi, T. Au-Yeung,
C. W. Yip, X. Yao, A. B. C. Chan, Adv. Synth. Catal.
2004, 346, 723–726; b) C. Drago, L. Caggiano, R. F. W.
Jackson, Angew. Chem. 2005, 117, 7387–7389; Angew.
Chem. Int. Ed. 2005, 44, 7221–7223; c) Q. Zeng, H.
Wang, T. Wang, Y. Cai, W. Weng, Y. Zhao, Adv. Synth.
Catal. 2005, 347, 1933–1936.
General Procedure for the Asymmetric Oxidation of
1,3-Dithianes Derived from Aldehydes and Ketones
To a solution of VOACHTUNRGTNEUNG(acac)2 (0.01 mmol) in CH2Cl2 (2 mL), a
chiral ligand (0.015 mmol) was added at room temperature.
The mixture was stirred for 10 min and then the sulfide sub-
strate (1 mmol) was added. After the solution was stirred
for another 2 min and cooled to 08C, 30% H2O2 (1.1 equiv.)
was slowly added. The mixture was stirred smoothly
(200 rpm) at 258C for 16 h. After the reaction was complete
(monitored by TLC), the organic layer was separated,
washed with brine and dried over Na2SO4. The solvent was
removed under reduced pressure to afford the crude prod-
uct which was purified by flash column chromatography on
silica gel to give the desired product.
Acknowledgements
[12] C. Bolm, F. Bienewald, Synlett 1998, 1327–1328.
[13] F. Di Furia, G. Licini, G. Modena, Gazz. Chim. It,
1990, 120, 165–170.
We thank the Natural Science Foundation of China (20972198)
and the Ministry of Science and Technology of China (No.
2009ZX09501-017) for financial support of this study.
[14] M. Corich, F. Di Furia, G. Licini, G. Modena, Tetrahe-
dron Lett, 1992, 33, 3043–3044.
[15] P. C. B. Page, R. D. Wilkes, E. S. Namwindwa, M. J
Witty, Tetrahedron 1996, 52, 2125–2154.
[16] V. Aggarwal, Z. Gultekin, R. S. Grainger, H. Adams,
P. L. Spargo, J. Chem. Soc. Perkin Trans. 1 1998, 2771–
2782.
[17] V. Alphand, N. Gaggero, S. Colonna, P. Pasta, R. Fur-
stoss, Tetrahedron 1997, 53, 9695–9706.
[18] T. Tanaka, B. Saito, T. Katsuki, Tetrahedron Lett. 2002,
43, 3259–3262.
[19] a) P. C. B. Page, A. M. Z. Slawin, D. Westwood, D. Wil-
liams, J. Chem. Soc. Perkin Trans. 1 1989, 185–187;
b) P. C. B. Page, S. M. Allin, E. W. Collington, R A. E.
Carr, Tetrahedron Lett, 1994, 35, 2427–2430; c) P. C. B.
Page, D. Westwood, A. M. Z. Slawin, D. J. Williams, J.
Chem. Soc. Perkin Trans. 1 1989, 1158–1160; P. C. B.
Page, J. C. Prodger, D. Westwood, Tetrahedron 1993,
49, 10355–10368; d) P. C. B. Page, J. C. Prodger, Synlett
1990, 460–462; e) P. C. B. Page, J. C. Prodger, M. B.
Hursthouse, M. Mazid, J. Chem. Soc. Perkin Trans. 1
1990, 167–169; f) P. C. B. Page, J. C. Prodger, Synlett
1991, 2, 84–86; g) P. C. B. Page, S. M. Allin, E. W. Col-
lington, R A. E. Carr, J. Org. Chem. 1993, 58, 6902–
6904.
References
[1] a) H. Pellissier, Tetrahedron 2006, 62, 5559–5601; b) I.
Fernꢂndez, N. Khiar, Chem. Rev. 2003, 103, 3651–3705;
c) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org.
Chem. 2003, 68, 150–155; d) S. Renfrey, J. Feather-
stone, Nat. Rev. Drug. Discov. 2002, 1, 175–176; e) P.
Renaud, M. Gerster, Angew. Chem. 1998, 110, 2704–
2722; Angew. Chem. Int. Ed. 1998, 37, 2562–2579;
f) M. C. CarreÇo, Chem. Rev. 1995, 95, 1717–1760.
[2] a) A. J. Walker, Tetrahedron: Asymmetry 1992, 3, 961–
998; b) A. V. Mashkina, Sulfur Rep. 1991, 10, 279–288.
[3] a) S. Superchi, C. Rosini, Tetrahedron: Asymmetry
1997, 8, 349–352; b) M. I. Donnoli, S. Superchi, C.
Rosini, J. Org. Chem. 1998, 63, 9392–9395; c) L. J. P.
Martyn, S. Pandiaraju, A. K. Yudin, J. Organomet.
Chem. 2000, 603, 98–104; d) X. Wang, X. Wang, H.
Guo, Z. Wang, K. Ding, Chem. Eur. J. 2005, 11, 4078–
4088.
[4] a) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189–214;
b) M. Cavazzini, G. Pozzi, S. Quici, I. Shepperson, J.
Mol. Catal. A: Chem. 2003, 204, 433–441.
[20] Y. Wu, J. Liu, X. Li, A. S. C. Chan, Eur. J. Org. Chem.
[5] a) J. T. Groves, P. Viski, J. Org. Chem. 1990, 55, 3628–
3634; b) Y. Naruta, F. Tani, K. Maruyama, J. Chem.
Soc. Chem. Commun. 1990, 19, 1378–1380; c) J.
Legros, C. Bolm, Angew. Chem. 2004, 116, 4321–4324;
Angew. Chem. Int. Ed. 2004, 43, 4225–4228; d) J.
Legros, C. Bolm, Angew. Chem. 2003, 115, 5645–5647;
Angew. Chem. Int. Ed. 2003, 42, 5487–5489.
[6] a) B. Pelotier, M. S. Anson, I. B. Campbell, S. J. F. Mac-
Donald, G. Priem, R. F. W. Jackson, Synlett 2002, 7,
1055–1060; b) Y. C. Jeong, S. Choi, Y. D. Hwang, K. H.
Ahn, Tetrahedron Lett. 2004, 45, 9249–9252; c) A. H.
Vetter, A. Berkessel, Tetrahedron Lett. 1998, 39, 1741–
1744.
2009, 16, 2607–2610.
[21] a) F. A. Carey, O. D. J. Dailey, W. C. Hutton, J. Org.
Chem. 1978, 43, 96–101; b) O. Samuel, B. Ronan, H. B.
Kagan, J. Organomet. Chem. 1989, 370, 43–50.
[22] a) J. Sun, C. Zhu, Z. Dai, M. Yang, Y. Pan, H. Hu, J.
Org. Chem. 2004, 69, 8500–8503; b) I. Mohammadpoor-
Baltork, M. Hill, L. Caggiano, R. F. W. Jackson, Synlett
2006, 3540–3544.
[23] A. Lattanzi, S. Piccirillo, A. Scettri, Eur. J. Org. Chem.
2006, 13, 713–718.
[24] G. Santoni, M. Mba, M. Bonchio, W. A. Nugent, C.
Zonta, G. Licini, Chem. Eur. J. 2010, 16, 645–654.
1712
ꢁ 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2011, 353, 1707 – 1712