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Citation: LI Wei-Jie, XU Zun-Le. Synthesis and Application of 3,4-Dihydroxy-2,5-bis(2'-(4'-substitutedoxazolinyl)) furan[J]. Chinese Journal of Applied Chemistry, ;2005, 22(12): 1316-1319. shu

Synthesis and Application of 3,4-Dihydroxy-2,5-bis(2'-(4'-substitutedoxazolinyl)) furan

LI Wei-Jie ^a,, ,
XU Zun-Le ^b

1.
a Multidisciplinary Research Center, Shantou University, Shantou 515063;
2.
b School of Chemistry and Chemical Engineering, Zhongshan University, Guangzhou

Corresponding author: LI Wei-Jie,
Received Date: 28 January 2005
Available Online: 26 June 2005
Fund Project: 汕头大学自然科学基金博士启动基金资助(240-072009) (240-072009)

Three 3,4-dihydroxy-2,5-bis(2'-(4'-substitutedoxazolinyl))furans were synthesized in yields of(90%~94%) from 3,4-dihydroxy-2,5-furan dicarboxylic acid or its dimethyl ester with chiral β-amino alcohol via a one-step reaction,and their chemical structures were determined by ¹H NMR,IR,MS,and elemental analysis.With these chiral bisoxazoline ligands,the asymmetric reduction of β-acetonaphthalene by KBH₄ or NaBH₄ was preliminarily studied.The enantiomeric excess of the reduction product was up to 83.2% using cyclohexane as the solvent,n(ligand):n(reductive agent):n(β-acetonaphthalene)=0.04:1.6:1,and 72 h reaction time at 0℃,and furan-containing bisoxazoline with 4-benzyl on oxazoline rings exhibited higher enantioselectivity than congeneric bisoxazolines with 4-ethyl on oxazoline rings.
- dihydroxy-bis(substitutedoxazolinyl) furan,
- bisoxazoline,
- chiral reagent,
- asymmetric reduction,
- synthesis
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