Synthesis and applications of 3,4-dihydroxy-2,5-bis-(2 '-(4'-substituted-oxazolinyl)) furan

• 来源期刊: 中国高等学校学术文摘·化学
• 关键词: 3 4-dihydroxy-2 5-bis(2'-(4'-substituted-oxazolinyl)furan bis(oxazoline) chiral reagent asymmetric reduction synthesis
• 年，卷（期）: 2006,（3）
• 页码范围: 292-295
• 页数: 4页
• 语种: 英文

摘要

Three 3,4-dihydroxy-2,5-bis-(2'-(4'-substituted-oxazolinyl)) furans were synthesized at 90%-94% yields from reaction of 3,4-dihydroxyfuran-2,5-dicar-boxylic acid or its dimethyl ester with chiral β-amino alcohol via a one-step process.Their chemical structures were determined by 1H NMR,IR,MS,and elemental analysis.With these chiral bisoxazoline ligands,the asymmetric reductive reaction of β-acetonaphthalene with KBH4 or NaBH4 was preliminarily studied.The enantiomeric excess of the reduction product was up to 83.2% with cyclohexane as the solvent,the molar ratio of ligand:reductive agent:β-acetonaphthalene is 0.04:1.6:1,and 72-hours reaction time at 0℃.Furancontaining bisoxazoline with 4-benzyl on oxazoline rings exhibited higher enatioselectivity than congeneric bisoxazolines with 4-ethyl on oxazoline rings.