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Citation: XIANG Ji-Ming, FENG Xiao-Jin, LI Bao-Lin. Synthesis and Asymmetric Henry Reaction of Menthyl Phenylglyoxylate[J]. Chinese Journal of Applied Chemistry, ;2009, 26(7): 857-859. shu

Synthesis and Asymmetric Henry Reaction of Menthyl Phenylglyoxylate

1.
a Department of Chemistry, Ankang College, Ankang 725000;
2.
b School of Chemistry and Materials Science, and MOE Key Laboratory of Medicinal Plant Resource & Natural Pharmaceutical Chemistry, Shaanxi Normal University, Xi'an 710062

Corresponding author: XIANG Ji-Ming,
Received Date: 28 June 2008
Available Online: 20 August 2008
Fund Project: 教育部科学技术研究重点项目(105153) (105153)陕西省教育厅资助项目(01JK075) (01JK075)

In the presence of titanium(Ⅳ) ethoxide,chiral menthyl phenylglyoxylate was prepared via transesterification of ethyl phenylglyoxylate and the abundant natural chiral menthol,and the yield of the transesterification was 68%.In the auxiliaries of asymmetric factor,the menthyl R-2-hydroxy-2-phenyl-3-nitropropionate was synthesized by the Henry reaction with menthyl phenylglyoxylate and nitromethane,and the yield was 86%.Their structures were confirmed by IR,¹H NMR,¹³C NMR spectroscopy and elemental analysis.The enantioselectivity was analyzed by HPLC,and the enantiomeric excess(e.e) was 52.8%.
- α-ketoester,
- menthol,
- transesterification,
- asymmetric Henry reaction,
- menthyl R-hydroxy-phenyl-nitropropionate
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