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Citation: ZHANG Yong-Qiang, SHEN Zong-Xuan, ZHANG Ya-Wen. Synthesis and Application in Enantioselective Epoxidation of Chalcone of Chiral Quaternary Ammonium Salts Based on Cinchonine[J]. Chinese Journal of Applied Chemistry, ;2006, 23(11): 1233-1236. shu

Synthesis and Application in Enantioselective Epoxidation of Chalcone of Chiral Quaternary Ammonium Salts Based on Cinchonine

1.
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215123

Corresponding author: ZHANG Ya-Wen,
Received Date: 29 November 2005
Available Online: 26 January 2006
Fund Project: 江苏省有机合成重点实验室开放课题(JSK015) (JSK015)

A new chiral quaternary ammonium salt 1a was synthesized by the reaction of cinchonine and 2,4,6-trimethyl benzyl chloride.Etherification between 1a and benzyl bromide,allyl chloride,or methyl iodide give corresponding etherified quaternary ammonium salts 1b,1c,and 1d.In the presence of 1b,1c,or 1d(5%,molar fraction),chalcone was stereoselectively epoxidized by sodium hypochlorite with yields range from 89% to 92% and ee range from 58% to 63%.
- chiral phase-transfer catalyst,
- synthesis,
- etherification,
- asymmetric epoxidation,
- chalcone
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