Li Wei, Xu Zun
2005
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Journal
Chinese Journal of Applied Chemistry
Abstract
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 ~(1)H NMR,IR,MS,and elemental(analysis).With these chiral bisoxazoline ligands,the asymmetric reduction of β-acetonaphthalene by KBH_(4) or NaBH_(4) was preliminarily studied.The enantiomeric excess of the reduction product was up to 83.2% using cyclohexane as the solvent,n(ligand)∶[KG-*3/5]n(reductive agent)∶[KG-*3/5]n(β-acetonaphthalene)=0.04∶[KG-*3/5]1.6∶[KG-*3/5]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.