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Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones
Wang, Jin1; Liu, Han1; Du, Da-Ming1,2
刊名TETRAHEDRON-ASYMMETRY
2009-05-25
DOI10.1016/j.tetasy.2009.02.057
20期:5页:605-609
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology ; Physical Sciences
类目[WOS]Chemistry, Inorganic & Nuclear ; Chemistry, Organic ; Chemistry, Physical
研究领域[WOS]Chemistry
关键词[WOS]FRIEDEL-CRAFTS ALKYLATION ; ENANTIO-SELECTIVE ADDITION ; ENANTIOSELECTIVE REDUCTION ; BIS(OXAZOLINE) LIGANDS ; CHIRAL PHOSPHINAMIDES ; MICHAEL ADDITION ; AROMATIC KETONES ; FACILE SYNTHESIS ; AMIDE) LIGANDS ; SQUARIC ACID
英文摘要A series of bis-hydroxyamides were synthesized from diphenylamine-2,2'-dicarboxylic acid and chiral aminoalcohols. Their catalytic activity in asymmetric borane reduction was investigated. After the fine optimization of solvents, temperature, amount of borane complex, and the length of catalyst generating period, good to excellent yields (55-99%) and enantioselectivities (79-97% ee) can be achieved in the reduction of aromatic and alkyl prochiral ketones. A transition state structure was proposed on the basis of absolute configuration and controlled experiment. (C) 2009 Elsevier Ltd. All rights reserved.
语种英语
WOS记录号WOS:000266526100011
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被引频次:12[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/141446
专题中国科学院大连化学物理研究所
作者单位1.Peking Univ, Coll Chem & Mol Engn, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
2.Beijing Inst Technol, Sch Chem Engn & Environm, Beijing 100081, Peoples R China
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Wang, Jin,Liu, Han,Du, Da-Ming. Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones[J]. TETRAHEDRON-ASYMMETRY,2009,20(5):605-609.
APA Wang, Jin,Liu, Han,&Du, Da-Ming.(2009).Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones.TETRAHEDRON-ASYMMETRY,20(5),605-609.
MLA Wang, Jin,et al."Diphenylamine-derived bis-hydroxyamide catalyzed asymmetric borane reduction of prochiral ketones".TETRAHEDRON-ASYMMETRY 20.5(2009):605-609.
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