Citation: Ping Xue, Zhen-Zhen Kang, Xiao-Yong Lai, Guan-Qun Qu, Yuan-Yuan Li. Efficient transesterification resolution of 2-(4-chlorophenyl)- 4-hydroxytetrahydropyran with magnetically separable immobilized lipase[J]. Chinese Chemical Letters, ;2013, 24(12): 1112-1114. shu

Efficient transesterification resolution of 2-(4-chlorophenyl)- 4-hydroxytetrahydropyran with magnetically separable immobilized lipase

1.
State Key Laboratory Cultivation Base of Natural Gas Conversion, Ningxia University, Yinchuan 750021, China

Corresponding author: Ping Xue,
Received Date: 13 May 2013
Available Online: 12 June 2013
Fund Project:

We report an efficient kinetic resolution of racemic 2-(4-chlorophenyl)-4-hydroxytetrahydro-pyran (CLP-4-HTHP) via Pseudomonas cepacia lipase (PSL)-catalyzed transesterification, where PSL is immobilized on a core-shell MnFe₂O₄@SiO₂-(CH₂)₃-NH₂ carrier and used as a magnetically separable catalyst. The as-synthesized PSL/MnFe₂O₄@SiO₂-(CH₂)₃-NH₂ catalyst exhibits enhanced catalytic activity for resolving racemic CLP-4-HTHP to the corresponding optically pure (2R,4S)-CLP-4-HTHP compared to the free PSL. The ee_s for the former is 2.3 times larger than that for the latter under optimized conditions (99.4% and 44.1%, respectively), although the ee_p for them are same (99.2%). Meanwhile, the PSL/MnFe₂O₄@SiO₂-(CH₂)₃-NH₂ catalyst possesses a high saturate magnetization of 59.7 emu/g and could be easily recovered bymagnetic separation and reused. The catalytic activity in six recycling tests did not significantly decrease, suggesting its great potential for industrial applications.
- Optically pure 2-(4-chlorophenyl)-4-,
- hydroxytetrahydropyran,
- Magnetically immobilized lipase,
- Enanatioselectivity,
- Asymmetric transesterification
1. [1]
  [1] F. Perron, F. Kim, Albizati, Synthesis of 4-hetero-substituted pyranosides via dioxenium cation-olefin cyclization, J. Org. Chem. 52 (1987) 4128-4130.
2. [2]
  [2] M.M. Andrea, H.M.R. Hoffmann, Asymmetric synthesis of seven-carbon segments of the phorboxazoles and (-)-discodermolide: complementary route from racemic trans-2,4dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one, Tetrahedron 55 (1999) 4315-4324.
3. [3]
  [3] J.S. Yadav, M.S. Reddy, P. Purusho, et al., Stereoselective synthesis of anti-1,3-diol units via Prins cyclisation: application to the synthesis of (-)-sedamine, Tetrahedron Lett. 47 (2006) 4397-4401.
4. [4]
  [4] P. Xue, X.H. Yan, Z. Wang, Lipase immobilized on HOOC-MCF: a highly enantioselective catalyst for transesterification resolution of (R,S)-1-phenylethanol, Chin. Chem. Lett. 18 (2007) 929-932.
5. [5]
  [5] J.S. Yadav, B.V.S. Reddy, B. Padmavani, et al., Enzymatic kinetic resolution of racemic 4-tetrahydropyranols by Candida rugosa lipase, Tetrahedron Lett. 48 (2007) 4631-4633.
6. [6]
  [6] H. Deng, X.L. Li, Q. Peng, et al., Monodisperse magnetic single-crystal ferrite microspheres, Angew. Chem. Int. Ed. 44 (2005) 2782-2785.
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沈阳化工大学材料科学与工程学院沈阳 110142