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Citation: LIU Wen-Min, WANG Qiao-Feng, LIU Xue-Ying, ZHANG Sheng-Yong. Asymmetric Epoxidation of α,β-Enones Catalyzed by Chiral Pyrrolidinylmethanol Derivatives[J]. Chinese Journal of Applied Chemistry, ;2007, 24(8): 925-928. shu

Asymmetric Epoxidation of α,β-Enones Catalyzed by Chiral Pyrrolidinylmethanol Derivatives

1.
a College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang 473061;
2.
b Department of Pharmacy, the Fourth Military Medical University, Xi'an

Corresponding author: LIU Wen-Min,
Received Date: 20 November 2006
Available Online: 20 February 2007
Fund Project: 国家自然科学基金(20572131)资助项目 (20572131)

Five chiral β-amino alcohols were prepared from (S)-proline in an efficient manner and applied in the organocatalytic asymmetric epoxidation of α,β-enones.The effect of the catalyst structure,oxidant,solvent and reaction temperature on enantioselectivity was also studied.The results show that the catalyst structure,oxidant and solvent were important for the stereoselectivity and the conversion.However,the change in the enantioselectivity was not obvious when the reaction temperature was decreased from room temperature to -20℃.When tert-butyl hydroperoxide (TBHP) was used as the oxidant,and hexane as the solvent,at room temperature,(S)-2-(di-α-naphthylhydroxymethyl) pyrrolidine 2b was successfully applied in the organo-catalytic asymmetric epoxidation of α,β-enones with good yield and up to 84.6% enantiomeric excess.The structure of compound 4 was confirmed by ¹H NMR,and the e.e.values were determined by HPLC analysis on chiral columns.
- epoxide,
- chiral β-aminoalcohol,
- asymmetric catalysis,
- α,β-enone,
- L-proline derivative
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