G. Li et al.
dark brown solid product was isolated by filtration and washed and dried in an air
oven at 80 °C for 12 h.
Traditional procedure for synthesis of (3R,4R)-4-acetoxy-3-[(R)-1((t-
butyldimethylsilyl)oxy)-ethyl]-1-methoxyphenyl-2-azetidinone (1)
The reaction was conducted with 2 (0.026 mol), NaBrO3 (2 equiv), 4.15 % Cu-
OMS-2 (1.15 g), and NaOAc (1.5 equiv) in 60 ml acetic acid under air at 65 °C for
3 h. After removal of the solvent in vacuo, the residual products were dissolved by
ethyl acetate (100 ml). The organic layer was washed with water and brine, dried
over MgSO4, and concentrated under reduced pressure. The residue was dissolved
by methanol (100 ml), additional water (100 ml) was added dropwise over 20 min,
and the mixture was stirred for 0.5 h at 5 °C. The resulting precipitate was isolated
by filtration and dried in vacuo to give 1 as colorless crystals (8.5 g, 82 %). mp
1
76–77 °C; H NMR (CDCl3) d 0.07 (s, 3H, SiCH3), 0.10 (s, 3H, SiCH3), 0.75 (s,
9H, t-Bu), 1.34 (d, J = 6.0 Hz, 3H, CH3), 2.10 (s, 3H, COCH3), 3.18 (d, J = 3 Hz,
1H, CH3), 3.76 (s, 3H, OCH3), 4.34 (m, 1H, CH), 6.27 (s, 1H, CH3), 6.72 (d, J =
10.4 Hz, 2H, ArH), 7.24 (d, J = 10.4 Hz, 2 H, ArH). 13C NMR: 169.84, 163.55,
156.26, 129.46, 118.33, 114.24, 76.64, 65.33, 64.14, 55.42, 25.62, 22.35, 21.14,
17.79, -4.18, -5.05.
Acknowledgments We thank Zhejiang Hisoar Pharmaceutical Co., Ltd for providing raw materials.
This work was financially supported by the National Natural Science Foundation of China (20903047),
and the Opening Project of State Key Laboratory of Chemical Resource Engineer (Beijing University of
Chemical Technology).
References
1. H. Kwon, M.J. Lee, I.H. Lee et al., Bull. Korean Chem. Soc. 18, 475 (1997)
2. F. Cozzi, R. Annunziata, M. Cinquini et al., Chirality 10, 91 (1998)
3. G.I. Georg, J. Kant, H.S. Gill, J. Am. Chem. Soc. 109, 1129 (1987)
4. G. Zhou, Y. Guan, H. Tang et al., Res. Chem. Intermed. 38, 251 (2012)
5. M. Shiozaki, N. Ishida, Chem. Lett. 2, 169 (1983)
6. S.-I. Murahashi, T. Naota, T. Kuwabara, JACS 112, 7820 (1990)
7. G. Cainelli, P. Galletti, D. Giacomini, Tetrahedron Lett. 39, 7779 (1998)
8. M. Laurent, M. Ceresiat, J. Marchand-Brynaert, J. Org. Chem. 69, 3194 (2004)
9. J.M. Anderson, J.K. Kochi, J. Am. Chem. Soc. 92, 1651 (1970)
10. L. Li, P. Yu, J. Cheng et al., Chem. Lett. 41, 600 (2012)
11. X. Chen, X.-S. Hao, E. Charles et al., J. Am. Chem. Soc. 128, 6790 (2006)
12. F. Schurz, J. Bauchert, T. Merker et al., Appl. Catal. A 355, 42 (2009)
13. R. Wang, J. Li, Environ. Sci. Technol. 44, 4282 (2010)
14. H. Huang, S. Sithambaram, C. Chen et al., Chem. Mater. 22, 3664 (2010)
15. G.G. Xia, Y.G. Yin, W.S. Willis et al., J. Catal. 185, 91 (1999)
123